ABCDEFGHIJKLMNOPQRSTUVWXYZAAABACADAEAFAGAHAIAJAKALAMANAOAPAQARASATAUAVAWAXAYAZBABBBCBDBEBFBGBHBIBJBKBLBMBNBOBPBQBRBS
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YearAuthorScheme exampleTITTLEJOURNALABSTRACTUNV./INST.Published_dateNiCouplingComplexSpeicalReason to ignoreProposed
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Energy
Profile
F.Bond
Type
Coupling TypeLeaving Group class 1Leving group class 2Leaving group 1Leaving group 2R- Group ER-Group NUBaseBase ClassBase Sub ClassC-E bond strengthE_HammettNi CyCleRLS (estimated)LVGroupLigandSolventBaseAcidSaltAdditives
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NoteArticle cited (In our database)ReferencesCheck article cited itAdded/datePublication DatePublication YearC-N Activation?C-O ActivationPhotocatalysthydroCarbonylationVolumeIssueStart Page
3
144FALSEadsc.20040415010.1002/adsc.200404150https://sci-hub.wf/10.1002/adsc.200404150https://doi.org/10.1002/adsc.200404150NiC-O ActivationGerryTRUE72482004Tang, ZY
Room temperature nickel (0)-catalyzed Suzuki-Miyaura cross-couplings of activated alkenyl tosylates: Efficient synthesis of 4-substituted coumarins and 4-substituted 2(5H)-furanones
ADVANCED SYNTHESIS & CATALYSIS
Room temperature nickel(0)/tricyclohexylphosphine [Ni(0)/PCy3]-catalyzed Suzuki-Miyaura cross-couplings of 4-(p-toluenesulfonyloxy)coumarins and 4-(p-toluenesulfonyloxy)-2(5H)-furanone with arylboronic acids are described in this communcation. Our study shows that activated alkenyl tosylates possess higher activities than aryl tosylates in the Suzuki-Miyaura cross-couplings. The mild reaction conditions and the high efficiency of the Ni(0)/ PCy3 catalyst make it very useful in the synthesis of 4-substituted coumarins and 4-substituted 2(5H)-furanones, two families of biologically important molecules.
CUNY Coll Staten Isl
12/1/2004Csp2-Csp2_arE-NuOBOTsB(OH)2VinylArylK3PO4Ionic-PO4Weak0.36_10.1246/cl.2005.796,10.1002/ejoc.200900067,10.1002/adsc.201100151,10.1021/jacs.8b0213410.3390/ph15010104,10.1039/d1ob00797a,10.1002/ajoc.202100039,10.1002/cctc.202001347,10.1002/adsc.201801586,10.1007/s10600-019-02705-8,10.1021/acs.joc.8b02760,10.3390/molecules23102417,10.1021/jacs.8b02134,10.6023/cjoc201708058,10.1002/adsc.201700838,10.1246/cl.170466,10.1002/ejic.201601351,10.1002/adsc.201600349,10.1002/adsc.201600205,10.1039/c5ob02125a,10.1021/acs.joc.5b00800,10.1021/acs.joc.5b00364,10.6023/cjoc201408028,10.1002/ejoc.201403404,10.1039/c5cc01427a,10.1039/c4cc04377d,10.1002/jhet.1784,10.1016/j.tet.2013.11.056,10.1016/j.tet.2013.10.043,10.1016/j.tetlet.2013.04.123,10.1016/j.tet.2012.12.030,10.1039/c3cs35521g,10.1039/c3ra23188g,10.1055/s-0031-1290455,10.1021/jo301086k,10.1016/j.tetlet.2012.03.108,10.1021/jo202577m,10.1039/c2dt12187e,10.1039/c2cc34551j,10.1016/j.tet.2011.07.048,10.1002/adsc.201100151,10.1007/s12039-011-0092-5,10.1021/cr1002276,10.1039/c1cc12240a,10.1002/chem.201002273,10.1055/s-0030-1258324,10.1055/s-0030-1258116,10.1016/j.tetlet.2009.12.033,10.1016/j.tetlet.2009.10.096,10.1039/c004233a,10.1021/om900771v,10.1002/ejoc.200900581,10.1016/j.tet.2009.06.089,10.1002/adsc.200900287,10.1016/j.tetlet.2009.02.116,10.1002/ejoc.200900067,10.1002/jhet.96,10.1021/ol802239n,10.1021/ol802049t,10.1021/ja804672m,10.1002/aoc.1359,10.1021/jo7019064,10.1021/jo071117+,10.1016/j.tetlet.2007.05.119,10.1016/j.tetlet.2007.03.142,10.1016/j.tetlet.2006.10.156,10.1002/ejoc.200600469,10.1016/j.tetlet.2006.07.085,10.1002/adsc.200505409,10.1016/j.tetlet.2006.01.020,10.1021/jo052369i,10.1246/cl.2005.796,10.1021/jo0502549Kelly12/3/2021
4
72FALSEadsc.20100071010.1002/adsc.201000710https://sci-hub.wf/10.1002/adsc.201000710https://doi.org/10.1002/adsc.201000710NiC-O ActivationElaineTRUE407322011Han, FS
Highly Efficient Suzuki-Miyaura Coupling of Aryl Tosylates and Mesylates Catalyzed by Stable, Cost-Effective [1,3-Bis(diphenylphosphino)propane]nickel(II) Chloride [Ni(dppp)Cl-2] with only 1 mol% Loading
ADVANCED SYNTHESIS & CATALYSIS
We present a highly active, inexpensive, universally applicable, and markedly stable [1,3-bis(diphenylphosphino)propane]nickel(II) chloride [Ni(dppp)Cl-2] catalyst that is capable of effecting the Suzuki-Miyaura cross-coupling of the inherently less reactive but readily available aryl tosylates and mesylates with only 1 mol% loading and in the absence of extra supporting ligand. Under the optimized reaction conditions, cross-coupling of a wide range of activated, non-activated, and deactivated, as well as sterically hindered and heteroaromatic substrates (36 examples) could proceed efficiently to afford the coupled products in 53-99% yields. Consequently, the results presented in this work provide a significant advance in Suzuki-Miyaura cross-coupling in terms of generality, practicality, and cost which are key concerns in recent research regarding transition metal-catalyzed cross-couplings.
Chinese Acad Sci2/11/2011CONTAIN 3 componentsCsp2_ar-Csp2_arE-NuOBOMsB(OH)2ArylArylK3PO4Ionic-PO4Weak0.36TM10.1002/ejoc.201200444,10.1021/jacs.6b11412,10.1002/anie.201101461,10.1002/chem.201003403,10.1039/c4qo00321g,10.1021/jo2022982,10.1021/jo400553710.1002/aoc.5662,10.1016/j.chemphys.2018.09.018,10.1021/acs.organomet.7b00208,10.1038/s41570-017-0025,10.1021/jacs.6b11412,10.1016/j.jorganchem.2016.09.026,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1021/acs.orglett.5b01229,10.1021/acs.orglett.5b01466,10.1016/j.jorganchem.2015.01.009,10.6023/cjoc201408028,10.1021/ol503560e,10.1039/c4qo00321g,10.1039/c5ra12742d,10.1039/c5ra09765g,10.1016/j.catcom.2014.08.010,10.1002/ejoc.201402919,10.1002/ejoc.201402475,10.1007/s11426-014-5138-3,10.1016/j.tet.2014.04.059,10.6023/cjoc201307035,10.1002/asia.201300688,10.1002/aoc.3000,10.1021/jo4005537,10.1039/c3cs35521g,10.1002/adsc.201200364,10.1021/jo301270t,10.1002/chem.201103723,10.1002/ejoc.201200444,10.1002/ejoc.201200368,10.1021/jo2022982,10.1039/c2cc31718d,10.1039/c2cc15972d,10.1002/anie.201207428,10.1246/cl.2011.907,10.1002/adsc.201100101,10.1002/chem.201003403,10.1002/anie.20110146112/16/2021
5
111FALSEadsc.20110015110.1002/adsc.201100151https://sci-hub.wf/10.1002/adsc.201100151https://doi.org/10.1002/adsc.201100151NiC-O ActivationLongTRUE548262011Hu, QS
Room Temperature Nickel(II) Complexes [(4-MeOC6H4)Ni-(PCy3)(2)OTs and Ni(PCy3)(2)X-2]-Catalyzed Cross-Coupling Reactions of Aryl/Alkenyl Sulfonates with Arylboronic Acids
ADVANCED SYNTHESIS & CATALYSIS
Room temperature nickel(II) complexes [(4-MeOC6H4)Ni(PCy3)(2)OTs and Ni(PCy3)(2)X-2 (X=Cl, Br)]-catalyzed cross-coupling reactions of aryl/alkenyl sulfonates with arylboronic acids are described. The nickel(II) complex (4-MeOC6H4)Ni(PCy3)(2)OTs proved to be a general catalyst for the Suzuki-Miyaura cross-coupling reactions of aryl sulfonates with arylboronic acids. By limiting the amount of the water in the initial catalytically active Ni(0) species generation stage, Ni(PCy3)(2)X-2 (X=Cl, Br) could also be efficient catalysts for the cross-coupling reactions a variety of aryl/activated alkenyl tosylates with arylboronic acids. The mild reaction condition, the easy availability of the catalysts and excellent coupling yields make these catalyst systems potentially useful in organic synthesis.
CUNY8/1/2011Csp2_ar-Csp2_arE-NuOBOTsB(OH)2ArylArylK3PO4Ionic-PO4Weak0.36TM10.1055/s-0036-1588845,10.1021/ol403209k,10.1021/jacs.6b11412,10.1021/jo3001194,10.1021/jo501291y,10.1021/jo300547v,10.1021/ol503061c,10.1021/acs.orglett.6b0139810.1002/ajoc.202100039,10.1002/cctc.202001347,10.2174/1385272824666200211114540,10.1002/adsc.201801586,10.1007/s10600-019-02705-8,10.1002/slct.201804039,10.1039/c8nj05503c,10.1016/j.tet.2018.10.025,10.1021/acs.organomet.8b00589,10.3390/molecules23102417,10.6023/cjoc201803053,10.6023/cjoc201708058,10.1002/ejoc.201701300,10.1002/hc.21397,10.1055/s-0036-1588845,10.1021/jacs.6b11412,10.1021/acs.joc.6b02093,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1021/acs.orglett.6b01398,10.1002/adsc.201600205,10.1002/adsc.201500461,10.1002/ejoc.201500610,10.1016/j.jorganchem.2015.04.019,10.1021/acs.orglett.5b01466,10.1016/j.jorganchem.2015.01.009,10.6023/cjoc201408028,10.1021/ol503560e,10.1039/c5ra09765g,10.1021/ol503061c,10.1016/j.tetlet.2014.01.148,10.1007/s11426-014-5138-3,10.1021/jo501291y,10.1016/j.tet.2014.04.059,10.1021/cs4009946,10.1021/ol403209k,10.6023/cjoc201307035,10.1016/j.tet.2013.10.089,10.1002/ejoc.201300592,10.1002/asia.201300688,10.1016/j.tetlet.2013.04.123,10.1002/aoc.3000,10.1039/c3cs35521g,10.1039/c3ra23188g,10.1055/s-0031-1290455,10.1021/jo301270t,10.1021/jo300547v,10.1002/ejoc.201200368,10.1021/jo3001194,10.1021/jo202577m,10.1039/c2cc18150a Long 12/15/2021
6
44FALSEadsc.20110024110.1002/adsc.201100241https://sci-hub.wf/10.1002/adsc.201100241https://doi.org/10.1002/adsc.201100241NiC-O ActivationKellyTRUE321132011Tang, G
Synthesis of alpha-Hydroxy Carboxylic Acids via a Nickel(II)-Catalyzed Hydrogen Transfer Process
ADVANCED SYNTHESIS & CATALYSIS
A new catalytic system for beta-alkylation of lactic acid with primary alcohols has been developed. In the presence of nickel(II) acetate tetrahydrate [Ni(OAc)(2)(H(2)O)(4)] and base, lactic acid reacts with primary alcohols to afford the corresponding coupled alpha-hydroxy carboxylic acids in good to excellent yields via a hydrogen transfer process without any hydrogen acceptor or hydrogen donor.
Natl Tsing Hua Univ8/1/2011xCsp2_ar-Csp3-ring(s)E-NuOHOHHArylBenzylIonic-ORStrong-0.81_xxx10.1021/jacs.9b0328010.3390/polym14020231,10.1039/d1dt02849a,10.1021/acs.organomet.1c00328,10.1021/acs.organomet.1c00147,10.1039/d1ob00080b,10.1016/j.tet.2020.131245,10.1002/anie.202004758,10.1002/anie.202003104,10.1002/anie.201912055,10.1021/acs.orglett.9b02727,10.1002/cssc.201801660,10.1021/jacs.9b03280,10.1039/c9ob00418a,10.1002/anie.201810885,10.1016/j.tetlet.2018.01.077,10.1002/adsc.201700722,10.1002/chem.201701211,10.1016/j.tet.2015.11.016,10.1039/c6ob02010k,10.1002/anie.201410322,10.1039/c5cy00876j,10.1016/j.jbiotec.2013.06.015,10.1016/j.apcata.2013.04.040,10.1002/cssc.201200804,10.1002/asia.201201062,10.1002/adsc.201200996,10.6023/cjoc201208016,10.1039/c2gc35714c,10.1039/c1ob06743e,10.1039/c1ob06739g2/15/2022
7
8FALSEjacs.9b1120810.1021/jacs.9b11208https://sci-hub.wf/10.1021/jacs.9b11208https://doi.org/10.1021/jacs.9b11208NiDeletedGerryFALSE401172019
Rousseaux, SAL
#N/ANi-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
J AM CHEM SOC
Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.
Univ Toronto12/11/2019TRUETRUEFALSE_10.1002/anie.20220035210.1002/anie.202117843,10.1055/s-0041-1737761,10.1039/d1cc04996h,10.1002/asia.202100776,10.1007/s11419-021-00597-4,10.1021/acs.orglett.1c02285,10.1021/acs.orglett.1c02270,10.1002/chem.202101273,10.1021/jacs.1c05281,10.1039/c9cs00571d,10.1039/d1qo00162k,10.1016/j.ccr.2021.213889,10.1021/acs.orglett.1c00465,10.1016/j.chempr.2021.02.013,10.1021/jacs.1c00529,10.1021/acs.joc.0c02644,10.1016/j.tetlet.2020.152749,10.1016/j.catcom.2020.106175,10.1021/acs.chemrev.0c00301,10.2174/1570179418666210224124931,10.1021/acs.joc.0c02388,10.1039/d0qo00775g,10.1016/j.tet.2020.131388,10.1055/s-0040-1707300,10.1038/s41467-020-17939-2,10.1021/acs.chemrev.9b00682,10.1021/acs.joc.0c00458,10.1039/d0ob00737d,10.1021/jacs.0c03184,10.1021/acs.oprd.0c00104,10.1039/d0qo00282h,10.1021/jacs.0c02075,10.1039/d0ra01043j#N/ADEC 112019FALSEFALSEFALSEFALSE1414919257
8
9FALSEacs.orglett.9b0449710.1021/acs.orglett.9b04497https://sci-hub.wf/10.1021/acs.orglett.9b04497https://doi.org/10.1021/acs.orglett.9b04497NiC-N ActivationGerryTRUE362#N/A2020Matsuo, Y
Nickel-Catalyzed Deaminative Acylation of Activated Aliphatic Amines with Aromatic Amides via C-N Bond ActivationORG LETT
Deaminative functionalization of aliphatic primary amines has great synthetic utility. Herein, we describe a Ni-catalyzed reductive deaminative cross-electrophile coupling reaction between Katritzky salts and aromatic amides. This work provides examples of the synthesis of various ketones from alkylpyridinium salts, including both primary and secondary alkylamines. Given its mild reaction conditions and high functional group tolerance, this cross-coupling strategy is expected to be useful for late-stage functionalization of complex compounds.
Univ Sci & Technol China
2/7/2020Csp2-Csp3E-ENN
pyrrolidine-2,5-dione
2,4,6-Tris(4-Methoxyphenyl)Pyridinium+BF4-
Carbonyl
Alkyl#N/ANo Base_10.1038/s41467-021-25222-1,10.1002/anie.20200227110.1002/adsc.202200003,10.1039/d1cs01084k,10.1039/d1gc04184c,10.1002/anie.202114146,10.1002/hlca.202100158,10.1002/anie.202114731,10.1021/jacs.1c10150,10.1002/adsc.202100940,10.1021/acs.orglett.1c02458,10.1002/asia.202100691,10.1038/s41467-021-25222-1,10.1039/d1cc03292e,10.1021/acs.joc.1c01110,10.1002/ejic.202100347,10.1039/d1sc01217g,10.1039/d1qo00037c,10.1039/d1sc00986a,10.1021/acs.orglett.1c00178,10.1039/d0cc07632e,10.1002/ejoc.202001193,10.1002/chem.202004840,10.1039/d0ob01807d,10.2174/1570179418666210224124931,10.7536/PC200607,10.1021/acscatal.0c03341,10.1021/jacs.0c08595,10.1055/s-0040-1707301,10.1016/j.trechm.2020.08.001,10.1021/acs.orglett.0c01592,10.1002/anie.202002271,10.1039/d0cc01333a,10.1021/acs.orglett.0c00554,10.1021/acs.orglett.0c00885,10.1021/acs.orglett.0c00442Long2/23/2022
9
10FALSEs-0037-161008410.1055/s-0037-1610084https://sci-hub.wf/10.1055/s-0037-1610084https://doi.org/10.1055/s-0037-1610084NiC-N ActivationGerryTRUE414272018Watson, MP
Vinylation of Benzylic Amines via C-N Bond Functionalization of Benzylic Pyridinium Salts
SYNTHESIS-STUTTGART
Cross-couplings of benzylic pyridinium salts and vinylboronic acids or esters have been developed. Via benzylic pyridinium intermediates, benzylic amines can be engaged in these cross-couplings through C-N bond functionalization. This method boasts mild reaction conditions and excellent tolerance for heteroaryl substituents and a range of functional groups.
Univ Delaware8/1/2018Csp3-ring(s)-Csp2E-NuNB
Triphenylpyridinium+BF4-
B(OH)2BenzylVinylIonic-PO4_10.1021/jacs.9b05224,10.1021/jacs.9b00111,10.1021/acs.orglett.9b04497,10.1021/acs.orglett.9b0101410.1021/acs.orglett.2c00317,10.1055/s-0040-1719881,10.1002/adsc.202100940,10.3390/molecules26195947,10.1021/acs.joc.1c01555,10.1021/acs.orglett.1c02458,10.1021/acscatal.1c01860,10.1002/cctc.202100672,10.1016/j.tetlet.2021.153071,10.1021/acs.orglett.1c00178,10.1002/ejoc.202001193,10.1039/d0ob01807d,10.1021/acscatal.0c03341,10.1021/jacs.0c08595,10.1021/acs.orglett.0c01592,10.1021/acs.orglett.0c00554,10.1002/anie.201911660,10.1002/chem.202000412,10.1021/acs.orglett.9b04497,10.1055/s-0039-1690703,10.1039/c9qo01175g,10.1021/acs.orglett.9b03899,10.1021/acs.orglett.9b03284,10.1039/c9sc03765a,10.1021/acscatal.9b03084,10.1021/acs.orglett.9b02643,10.6023/A19040121,10.1002/adsc.201900576,10.1021/acs.orglett.9b02534,10.1021/jacs.9b05224,10.1002/chem.201901397,10.1038/s41929-019-0292-9,10.1021/acs.orglett.9b01014,10.1002/anie.201814452,10.1002/anie.201813689,10.1021/jacs.9b00111,10.1021/acscatal.8b04191,10.1021/acscatal.8b03437,10.1002/anie.201809608,10.1021/jacs.8b07103Long2/23/2022
10
11FALSEanie.20181452410.1002/anie.201814524https://sci-hub.wf/10.1002/anie.201814524https://doi.org/10.1002/anie.201814524NiC-H Activation10-FebFALSE462#N/A2019Baran, PS#N/AQuaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents
ANGEW CHEM INT EDIT
This work bridges a gap in the cross-coupling of aliphatic redox-active esters with aryl zinc reagents. Previously limited to primary, secondary, and specialized tertiary centers, a new protocol has been devised to enable the coupling of general tertiary systems using nickel catalysis. The scope of this operationally simple method is broad, and it can be used to simplify the synthesis of medicinally relevant motifs bearing quaternary centers.
Scripps Res2/18/2019TRUETRUEFALSE_10.1002/anie.202002271,10.1038/s41467-021-25222-110.1039/d1sc06422c,10.1039/d1sc05605k,10.1021/jacs.1c11170,10.1002/anie.202114731,10.1021/jacs.1c10150,10.1021/jacs.1c08157,10.1021/acs.joc.1c01625,10.1016/j.tetlet.2021.153290,10.1039/d1sc02642a,10.1073/pnas.2108881118,10.1021/jacs.1c03007,10.1038/s41598-021-88493-0,10.1039/d1sc00943e,10.1016/j.chempr.2020.12.024,10.1039/d1qo00210d,10.1039/d0cs01107j,10.1039/d0sc06385a,10.1021/acscatal.0c04756,10.1021/acs.orglett.0c02799,10.1055/s-0040-1707273,10.1039/d0sc02213f,10.1002/aoc.5662,10.1007/s00706-020-02613-6,10.1021/jacs.0c02237,10.1021/jacs.0c02355,10.6023/cjoc201911016,10.1021/jacs.0c00359,10.1002/anie.201911012,10.1021/acscatal.9b03596,10.1039/c9qo01073d,10.1002/chem.201905048,10.1039/c9qo01166h,10.1016/j.trechm.2019.08.004,10.1039/c9sc03070k,10.1021/acs.orglett.9b03018,10.1021/acscatal.9b02913,10.1039/c9cc05385a,10.1021/acs.orglett.9b02870,10.1002/anie.201909852,10.1002/anie.201909299,10.1021/jacs.9b03991,10.1021/jacs.9b02844,10.1021/jacs.9b02238#N/AFEB 182019FALSEFALSEFALSEFALSE5882454
11
74FALSEadsc.20140046010.1002/adsc.201400460https://sci-hub.wf/10.1002/adsc.201400460https://doi.org/10.1002/adsc.201400460NiC-O ActivationGerryTRUE435592014Iranpoor, N
Direct Nickel-Catalyzed Amination of Phenols via C-O Bond Activation using 2,4,6-Trichloro-1,3,5-triazine (TCT) as Reagent
ADVANCED SYNTHESIS & CATALYSIS
2,4,6-Trichloro-1,3,5-triazine (TCT) was used as an efficient and mild reagent for the direct nickel-catalyzed amination of phenols. This reagent can promote amination of phenols via the activation of the phenolic C-O bond. In this simple protocol, the in situ generated aryl C-O electrophile (Ar-O-TCT) reacts with the desired amine to produce the corresponding arylamine in the presence of a nickel catalyst. This strategy is general for a variety of substrates to give the related arylamines in moderate to good yields. This method was also applied for nickel-catalyzed amination of phenols for the synthesis of primary aromatic amines using the reaction of Ar-O-TCT and ammonium carbonate under mild reaction conditions. With this method, phenolic compounds are converted to their corresponding anilines under mild conditions.
Shiraz Univ10/13/2014Csp2_ar-Nsp3E-NuOHOHHAryl
Morpholine
K3PO4Ionic-PO4Strong-0.81_xxx10.1039/c7cc06717h,10.1021/acscatal.8b01879,10.1021/acscatal.6b00865,10.1021/acscatal.8b03436,10.1021/jacs.8b1340310.1039/d1ra08771a,10.1021/jacs.1c12622,10.3390/molecules26165079,10.1039/d1nj01762d,10.1021/acs.chemrev.0c00088,10.1002/cctc.202000876,10.1016/j.mcat.2020.110915,10.1039/d0sc01585g,10.1002/cjoc.201900506,10.1021/acs.joc.0c00424,10.1002/ejoc.202000117,10.1021/jacs.9b07887,10.1002/slct.201804066,10.1021/jacs.8b13403,10.1016/j.cclet.2018.09.009,10.1021/acscatal.8b03436,10.1021/acscatal.8b01879,10.1039/c8ob01034j,10.1021/acs.orglett.8b00974,10.1002/aoc.4273,10.1002/ajoc.201700450,10.1039/c7cc06717h,10.1002/ajoc.201700464,10.1021/acs.organomet.7b00314,10.1055/s-0036-1588806,10.3762/bjoc.13.146,10.1002/slct.201700923,10.1002/jhet.2652,10.1021/acs.organomet.6b00885,10.3390/polym9020037,10.1021/acscatal.6b02964,10.1002/adsc.201600336,10.1021/acscatal.6b00865,10.1002/ejoc.201501607,10.1039/c6ra14367a,10.1007/s13738-015-0682-0,10.1002/adsc.201500515,10.1021/acs.orglett.5b01466,10.1016/j.jorganchem.2015.01.009,10.1021/ja511622e,10.1021/ol503560e,10.1071/CH15459,10.1039/c5ra06753g1/5/2022
12
14FALSEjacs.7b0939410.1021/jacs.7b09394https://sci-hub.wf/10.1021/jacs.7b09394https://doi.org/10.1021/jacs.7b09394NiC-H ActivationFALSE1531472017Walsh, PJ#N/ATransition-Metal-Free Radical C(sp(3))-C(sp(2)) and C(sp(3))-C(sp(3)) Coupling Enabled by 2-Azaallyls as Super-Electron-Donors and Coupling-Partners
J AM CHEM SOC
The past decade has witnessed the rapid development of radical generation strategies and their applications in C-C bond-forming reactions. Most of these processes require initiators, transition metal catalysts, or organometallic reagents. Herein, we report the discovery of a simple organic system (2-azaallyl anions) that enables radical coupling reactions under transition-metal-free conditions. Deprotonation of N-benzyl ketimines generates semistabilized 2-azaallyl anions that behave as super-electron-donors (SEDs) and reduce aryl iodides and alkyl halides to aryl and alkyl radicals. The SET process converts the 2-azaallyl anions into persistent 2-azaallyl radicals, which capture the aryl and alkyl radicals to form C-C bonds. The radical coupling of aryl and alkyl radicals with 2-azaallyl radicals makes possible the synthesis of functionalized amine derivatives without the use of exogenous radical initiators or transition metal catalysts. Radical clock studies and 2-azaallyl anion coupling studies provide mechanistic insight for this unique reactivity.
Univ Penn11/15/2017TRUETRUEFALSEx_10.1021/acs.orglett.2c00140,10.1039/d2sc00500j,10.1021/acs.orglett.1c04042,10.1038/s41467-021-26767-x,10.1002/chem.202103096,10.1021/jacs.1c05764,10.1038/s41467-021-24027-6,10.1038/s41467-021-24144-2,10.1021/acs.orglett.1c01009,10.1021/acs.orglett.1c00835,10.1021/acsomega.1c01116,10.1039/d1qo00083g,10.1039/d0sc04822d,10.1039/d1sc00972a,10.1039/d0qo01488e,10.1021/acs.orglett.1c00135,10.1002/anie.202009288,10.1021/acs.joc.0c01020,10.1021/acscatal.0c04519,10.1021/acs.joc.0c02225,10.1039/d0sc00031k,10.1021/acs.orglett.0c01836,10.1021/jacs.0c02707,10.1002/adsc.201901553,10.1002/anie.201903726,10.1039/c9sc03354h,10.1021/acs.orglett.9b02550,10.1002/adsc.201900497,10.1055/s-0037-1611770,10.1002/ejoc.201900537,10.1021/acs.joc.9b00649,10.1021/acs.orglett.9b00655,10.1002/anie.201812369,10.1002/chem.201805320,10.1021/acscatal.8b03999,10.1039/c8qo00873f,10.1002/anie.201810061,10.1039/c8cc06408c,10.1021/acs.chemrev.8b00349,10.1021/acs.orglett.8b02536,10.1002/adsc.201800396,10.1039/c8qo00207j,10.1021/acssuschemeng.8b01472,10.1038/s41467-018-04095-x,10.1021/acs.orglett.8b00778,10.1021/acs.joc.8b00491,10.1039/c8sc00008e,10.1002/anie.201713079#N/ANOV 152017FALSEFALSEFALSEFALSE1394516327
13
240FALSEanie.20045376510.1002/anie.200453765https://sci-hub.wf/10.1002/anie.200453765https://doi.org/10.1002/anie.200453765NiC-O ActivationLong16-FebTRUE23461152004
Dankwardt, JW
Nickel-catalyzed cross-coupling of aryl Grignard reagents with aromatic alkyl ethers: An efficient synthesis of unsymmetrical biaryls
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
New substrates for biaryl synthesis: aromatic ethers undergo nickel-catalyzed cross-coupling with aryl Grignard reagents to give unsymmetrical biaryls in excellent yields (see scheme). Both the nature of the nickel catalyst and the choice of solvent are crucial for reaching high levels of conversion.
DSM Pharmaceut Chem
4/22/2004TRUETRUEFALSECsp2_ar-Csp3-ring(s)E-NuOMgOMeMgXArylBenzylNo baseNo BaseStrong-0.28_xxx10.1002/anie.200803814,10.1021/ol9028308,10.1021/acs.orglett.5b02200,10.1021/ja8056503,10.1039/c4cc08187k,10.1002/anie.200907359,10.1021/ja810157e,10.1039/c7cc06717h,10.1021/ol4011757,10.1021/ol9029534,10.1002/chem.201000420,10.1021/ol901217m,10.1002/chem.201103784,10.1021/jacs.7b04973,10.1002/anie.201607646,10.1039/c1sc00230a,10.1002/anie.201007325,10.1002/anie.201510497,10.1002/chem.201003731,10.1002/anie.200907287,10.1021/ol9001587,10.1021/jo1024464,10.1021/acs.organomet.5b00874,10.1021/acs.orglett.9b00242,10.1021/acscatal.8b03436,10.1021/ja903091g,10.1246/cl.2009.710,10.1021/jo070313d,10.1021/ja710944j,10.1002/anie.201402922,10.1021/acscatal.9b00744,10.1039/b718998b,10.1002/chem.201603436,10.1021/ja501093m,10.1021/jacs.0c06995,10.1021/acscatal.6b00801,10.1021/ja200398c,10.1021/ol503707m,10.1021/jacs.8b02134,10.1021/ol502583h,10.1021/jacs.7b02326,10.1002/anie.202012048,10.1021/ol203322v,10.1021/jacs.6b03253,10.1021/acscatal.1c04800,10.1246/cl.150936,10.1021/acscatal.7b01058,10.1021/ol302112q,10.1021/jacs.1c09797,10.1002/anie.200900329,10.1002/anie.201806790,10.1021/ol901978e,10.1021/ja907700e,10.1021/ol4031815,10.1021/acs.orglett.6b02656,10.1016/j.tet.2012.04.005,10.1021/ja210249h,10.1002/ejic.201900692,10.1038/s41929-020-00560-3,10.1002/chem.201003403,10.1002/chem.20150510610.1021/acscatal.1c04800,10.1021/jacs.1c09797,10.1002/aoc.6430,10.1021/acscatal.1c02790,10.1039/c9cs00571d,10.1055/a-1507-4153,10.1055/a-1503-6330,10.1021/jacs.1c03038,10.1038/s41929-020-00560-3,10.1055/a-1349-3543,10.1055/s-0040-1705986,10.1002/anie.202012048,10.1021/acs.orglett.0c03507,10.1002/chem.202004132,10.1016/j.molstruc.2020.128572,10.1021/acscatal.0c03334,10.1021/acs.chemrev.0c00088,10.1021/jacs.0c06995,10.1021/acs.orglett.0c02236,10.1021/acs.organomet.0c00338,10.1021/acs.joc.0c00530,10.1002/cjoc.201900506,10.1246/cl.200083,10.1016/j.heliyon.2020.e03446,10.1055/s-0039-1690764,10.1002/adsc.201901096,10.2174/1385272824666200211114540,10.1016/j.apcatb.2019.117936,10.1002/ejic.201900692,10.1039/c9dt00455f,10.1007/s13738-019-01615-4,10.1021/acs.joc.9b00598,10.1002/cjoc.201800575,10.1021/acscatal.9b00744,10.1055/s-0037-1611663,10.1021/acs.orglett.9b00242,10.1021/acs.organomet.8b00720,10.1007/3418_2018_19,10.1021/acs.accounts.8b00408,10.1021/acscatal.8b03436,10.1016/j.tet.2018.10.025,10.1021/acs.joc.8b02104,10.1038/s41557-018-0110-z,10.1002/cctc.201800898,10.1002/anie.201806790,10.1021/jacs.8b03669,10.1039/c8cc02325e,10.1016/j.jorganchem.2018.01.019,10.1021/acscatal.8b01224,10.1038/s41467-018-03928-z,10.1021/jacs.8b02134,10.1002/cjoc.201700664,10.1039/c7cc08709h,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.1039/c7cc06717h,10.1002/chem.201703266,10.1055/s-0036-1588568,10.1055/s-0036-1590985,10.1021/acs.organomet.7b00613,10.1021/jacs.7b04973,10.1021/acscatal.7b02025,10.1248/cpb.c17-00487,10.1021/acscatal.7b01058,10.1002/anie.201610203,10.1021/jacs.7b02326,10.1021/acs.organomet.7b00129,10.1021/acscatal.6b03344,10.1039/c6sc02895k,10.1021/jacs.6b10998,10.1021/acscatal.6b02964,10.1002/anie.201607646,10.1021/acs.orglett.6b02656,10.1002/ajoc.201600411,10.1002/chem.201604160,10.1002/chem.201603436,10.1021/acs.organomet.6b00638,10.1002/asia.201600972,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1021/jacs.6b03253,10.1002/anie.201510497,10.1002/chem.201504718,10.1002/chem.201505106,10.1021/acscatal.5b02058,10.1002/anie.201509133,10.1016/bs.adomc.2016.07.001,10.1039/c5sc03359d,10.1021/acscatal.5b02089,10.1016/j.ccr.2015.02.004,10.1039/c5ob02212f,10.1021/acs.organomet.5b00874,10.1246/cl.150936,10.1021/jacs.5b08621,10.1021/acs.organomet.5b00710,10.1246/bcsj.20150180,10.1002/chem.201502114,10.1002/adsc.201500515,10.1021/acs.orglett.5b02200,10.1002/ejoc.201500630,10.1021/acs.orglett.5b01229,10.1002/adsc.201500304,10.1021/acs.accounts.5b00051,10.1021/acs.orglett.5b00654,10.1002/ejic.201500148,10.1021/ar500345f,10.1002/anie.201409739,10.1021/ol503707m,10.1039/c5qo00001g,10.1039/C5QO00243E,10.1039/c4cc08187k,10.1039/c4cc10084k,10.1002/anie.201402922,10.1021/ol502583h,10.1021/jo501361k,10.1021/jo500619f,10.1038/nature13274,10.1016/j.tet.2014.03.061,10.1002/adsc.201301081,10.1021/ja501093m,10.1515/pac-2014-5038,10.1016/j.tetlet.2013.12.083,10.1002/anie.201304268,10.1039/c4cc04939j,10.1039/c4cs00206g,10.1002/ejoc.201301372,10.1021/ol4031815,10.1002/anie.201307028,10.1021/ol4011757,10.1021/ja312464b,10.1016/j.tetlet.2012.12.078,10.1021/ja311940s,10.1016/j.tetlet.2012.12.027,10.1007/3418_2012_42,10.1039/c3sc22242j,10.1039/c3ob27128e,10.1039/c3cs35521g,10.1002/ejoc.201200914,10.1021/op300236f,10.1039/c3ra44884c,10.1021/ol3029059,10.1002/adsc.201200364,10.1021/ol302112q,10.1021/om300323d,10.1016/j.tet.2012.04.005,10.1021/om300369f,10.1021/ol3009842,10.1021/ol300908g,10.1021/ol300671y,10.1021/ja301588z,10.1016/j.jphotochem.2012.02.008,10.1021/ja300326t,10.1021/ol203322v,10.1002/chem.201103784,10.1021/ja210249h,10.1039/c2cc34454h,10.1021/ja207759e,10.1246/cl.2011.1001,10.1002/cctc.201100181,10.1002/cctc.201100087,10.1021/ol2012007,10.1021/ja200398c,10.1126/science.1200437,10.1002/chem.201003731,10.1021/jo1024464,10.1002/chem.201003403,10.1021/cr100259t,10.1039/c0sc00498g,10.1002/anie.201007325,10.1002/anie.201103599,10.1039/c0cc05169a,10.1039/c1sc00230a,10.1002/chem.201002273,10.1021/ar100082d,10.1002/chem.201001478,10.1021/jo101718v,10.1021/ol1018739,10.1021/jo1007898,10.1021/ol9029534,10.1021/ol9028308,10.1002/anie.200907287,10.1002/anie.200907359,10.1002/chem.201000420,10.1021/ja907700e,10.1055/s-0029-1217032,10.1021/ol901978e,10.1021/om900460u,10.1021/ja9039289,10.1021/ol901217m,10.1021/ja903091g,10.1246/cl.2009.710,10.1021/ja810157e,10.1016/j.molcata.2009.02.003,10.1021/ja902829p,10.1021/ol9001587,10.1002/anie.200900329,10.1039/b914982a,10.1021/ja8056503,10.1016/j.tetlet.2008.08.002,10.1016/j.tetlet.2008.04.117,10.1021/ja710944j,10.1002/anie.200801447,10.1002/anie.200804146,10.1002/anie.200803814,10.1039/b718998b,10.1039/b801888j,10.1055/s-2007-983845,10.1021/jo070313d,10.1021/ja0713431,10.1016/j.molcata.2006.09.039,10.1021/ja067612p,10.1016/j.molcata.2006.06.004,10.1016/j.ccr.2006.02.031,10.1002/ejic.200500685,10.1016/j.jorganchem.2005.09.010,10.1021/ja056327n,10.1021/ol051896l,10.1002/ejoc.200500279,10.1055/s-2005-871571,10.1055/s-2005-869856,10.1016/j.jorganchem.2004.10.037,10.1002/anie.200461444Kelly11/11/20212004FALSEFALSEFALSEFALSE43182428
14
250FALSEanie.20080144710.1002/anie.200801447https://sci-hub.wf/10.1002/anie.200801447https://doi.org/10.1002/anie.200801447NiC-O ActivationShihongTRUE34689892008Chatani, N
Nickel-catalyzed cross-coupling of aryl methyl ethers with aryl boronic esters
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
To COMe and go: The title reaction, involving cleavage of a COMe bond, is demonstrated for the coupling of aryl methyl ethers on fused aromatic systems, such as naphthalene and phenanthrene, as well as anisoles containing electron-withdrawing groups with a wide range of boronic esters. cod=cycloocta-1,5-diene, Cy=cyclohexyl.
Osaka Univ6/9/2008TRUETRUEFALSECsp2_ar-Csp2_arE-NuOBOMeB(nep)ArylArylCsFIonic-FStrong-0.28_xx10.1021/acscatal.7b01058,10.1002/anie.200907287,10.1021/ol302112q,10.1021/ja8056503,10.1021/ol9029534,10.1021/ja903091g,10.1021/jacs.6b03253,10.1002/anie.201101191,10.1002/anie.201806790,10.1002/adsc.201400460,10.1021/jacs.7b04973,10.1021/jo4005537,10.1021/ol4011757,10.1021/ol401727y,10.1002/anie.201402922,10.1021/acs.orglett.9b00242,10.1021/acs.orglett.5b02200,10.1021/ol4031815,10.1002/anie.201007325,10.1002/anie.201403823,10.1002/chem.201603436,10.1021/ja2084509,10.1021/ja5029793,10.1021/ol9001587,10.1021/acscatal.9b00744,10.1021/ol502583h,10.1021/ol901217m,10.1021/acs.orglett.6b01398,10.1021/jo2022982,10.1021/acscatal.8b03436,10.1039/c1cc11193k,10.1021/ol203322v,10.1021/jacs.9b00097,10.1021/jo300547v,10.1021/acs.orglett.6b02265,10.1055/s-0036-1588845,10.1021/jacs.6b11412,10.1002/anie.201510497,10.1021/ja907700e,10.1002/anie.200803814,10.1021/acs.joc.6b01627,10.1021/jacs.7b04279,10.1039/c5sc02942b,10.1002/anie.201607646,10.1002/anie.202012048,10.1002/ejoc.201001519,10.1021/acs.joc.8b02498,10.1039/c4cc08426h,10.1002/anie.202103327,10.1021/ja200398c,10.1021/acscatal.6b00801,10.1021/jo3001194,10.1021/acs.orglett.6b02656,10.1246/cl.150936,10.1021/ol901978e,10.1002/anie.200907359,10.1021/acs.orglett.5b03151,10.1002/adsc.201000710,10.1002/ejoc.201000147,10.1002/chem.201000420,10.1016/j.tet.2012.04.005,10.1002/chem.201103784,10.1021/cs501045v,10.1021/ol503707m,10.1002/anie.201511486,10.1021/ja210249h,10.1002/chem.201003403,10.1246/cl.2009.710,10.1021/om300566m,10.1021/jo202037x,10.1021/acs.orglett.6b00819,10.1039/c1sc00230a,10.1002/ejoc.200900067,10.1021/jacs.7b02326,10.1002/chem.201003731,10.1002/chem.200902785,10.1002/ejoc.201200444,10.1021/ja906477r,10.1021/jo1024464,10.1002/anie.201101461,10.1039/c4cc08187k,10.1039/c0cc03107k,10.1002/anie.200900329,10.1002/anie.201412051,10.1021/ol9028308,10.1021/jo2000034,10.1021/ol101592r,10.1039/c7cc06717h,10.1021/ja810157e10.1021/acs.orglett.2c00267,10.1039/d1gc04556c,10.1039/d1dt02986j,10.1021/acs.orglett.1c03048,10.1007/s10562-021-03799-y,10.1039/d1ob01619a,10.1002/hlca.202100089,10.1039/d1qo00811k,10.1039/c9cs00571d,10.1002/tcr.202100142,10.1039/d1qo00656h,10.1055/a-1507-6419,10.1055/a-1507-4153,10.1002/anie.202103327,10.1021/jacs.1c03038,10.1021/acs.accounts.1c00096,10.1039/d0nj05711h,10.1246/bcsj.20200277,10.1055/a-1349-3543,10.1038/s41467-020-19944-x,10.1002/anie.202012048,10.1021/acs.orglett.0c03507,10.1002/chem.202004132,10.1021/acscatal.0c03334,10.1021/acs.chemrev.0c00088,10.1021/acs.orglett.0c02236,10.1016/j.mcat.2020.110915,10.1021/jacs.0c05730,10.1039/d0cc02142c,10.1039/d0sc01585g,10.1002/aoc.5662,10.1002/cjoc.201900506,10.1246/cl.200083,10.1021/jacs.0c00283,10.1016/j.jpcs.2019.109256,10.1016/j.heliyon.2020.e03446,10.1055/s-0039-1690764,10.1021/acs.organomet.9b00672,10.1039/c9qo01095e,10.2174/1385272824666200211114540,10.1021/acs.joc.9b02154,10.1021/acs.orglett.9b03170,10.1016/j.isci.2019.08.021,10.1002/anie.201908336,10.1021/acs.orglett.9b02504,10.1016/j.jcat.2019.07.026,10.1021/acs.orglett.9b02050,10.21577/0103-5053.20190067,10.1039/c9dt00455f,10.1002/anie.201902315,10.1038/s41467-019-09766-x,10.1021/jacs.9b00097,10.1021/acscatal.9b00744,10.1002/adsc.201801085,10.1021/acs.orglett.9b00242,10.1021/acs.organomet.8b00720,10.1007/3418_2018_19,10.1021/acs.accounts.8b00408,10.1021/acscatal.8b03436,10.1016/j.tet.2018.10.025,10.1021/acs.joc.8b02498,10.1021/acs.joc.8b02104,10.1021/acs.organomet.8b00199,10.1002/adsc.201800729,10.1021/acs.jafc.8b03792,10.1039/c8cc03665a,10.1002/anie.201806790,10.1021/acs.orglett.8b01696,10.1021/jacs.8b04479,10.1021/acscatal.8b00933,10.1016/j.jorganchem.2018.01.019,10.1021/acs.orglett.8b00755,10.1021/acscatal.8b01224,10.1038/s41467-018-03928-z,10.1021/acs.orglett.8b00674,10.1002/cjoc.201700664,10.1021/acs.orglett.8b00080,10.1039/c7cc08709h,10.1039/c7cy01205e,10.1021/acs.joc.7b02588,10.1039/c8ra03754j,10.1039/c7cc06717h,10.1002/chem.201703266,10.1055/s-0036-1589093,10.1055/s-0036-1588568,10.1055/s-0036-1590985,10.1021/acscatal.7b03465,10.1002/ajoc.201700464,10.1055/s-0036-1590962,10.1002/anie.201706982,10.1021/jacs.7b04973,10.1248/cpb.c17-00487,10.1021/jacs.7b04279,10.1055/s-0036-1588845,10.1021/acs.orglett.7b01370,10.1021/jacs.7b03159,10.1021/acscatal.7b01058,10.1002/anie.201610203,10.1021/jacs.7b02326,10.1021/acs.organomet.7b00208,10.1021/acscatal.6b03344,10.1039/c6nj02887j,10.1021/jacs.6b10998,10.1021/jacs.6b11412,10.1021/acscatal.6b02964,10.1039/c7ra02549a,10.1002/anie.201607646,10.1021/acs.orglett.6b02656,10.1016/j.jorganchem.2016.09.026,10.1002/chem.201604160,10.1246/cl.160712,10.1002/chem.201603436,10.1021/acs.joc.6b01627,10.1021/acscatal.6b01956,10.1002/asia.201600972,10.1021/acs.orglett.6b02265,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1021/acs.orglett.6b01398,10.1002/anie.201601914,10.1021/acs.orglett.6b00819,10.1021/jacs.6b03253,10.1002/anie.201510497,10.1021/ac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Long 11/5/20212008FALSEFALSEFALSEFALSE47264866
15
17FALSEja209235d10.1021/ja209235dhttps://sci-hub.wf/10.1021/ja209235dhttps://doi.org/10.1021/ja209235dNiC-H ActivationLongTRUE10910662011Jamison, TF
Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins
J AM CHEM SOC
Nickel-catalyzed intermolecular benzylation and heterobenzylation of unactivated alkenes to provide functionalized allylbenzene derivatives are described. A wide range of both the benzyl chloride and alkene coupling partners are tolerated. In contrast to analogous palladium-catalyzed variants of this process, all reactions described herein employ electronically unbiased aliphatic olefins (including ethylene), proceed at room temperature, and provide 1,1-disubstituted olefins over the more commonly observed 1,2-disubstituted olefins with very high selectivity.
MIT11/30/2011TRUETRUEFALSECsp3-ring(s)-Csp2E-NuXHClHBenzylVinylNitrogenNitrogen(neutral)_10.1021/ja2084509,10.1021/jacs.9b03280,10.1021/ja5026485,10.1002/anie.201308391,10.1039/d1cc00634g,10.1002/anie.201810757,10.1002/anie.201108350,10.1021/ja3089422,10.1002/anie.201710241,10.1002/anie.20201103610.1002/adsc.202200096,10.1039/d1cc05949a,10.1039/d1ob01874d,10.1021/jacs.1c05661,10.1021/jacs.1c03228,10.1021/acscatal.1c00951,10.1039/d1cc00634g,10.1038/s41467-021-21270-9,10.1002/anie.202011036,10.1002/cctc.202001425,10.1038/s41467-020-19508-z,10.1002/adsc.202000820,10.1039/d0cc03966g,10.1002/cptc.202000061,10.1002/slct.202000814,10.1016/j.tet.2020.131201,10.1021/acs.orglett.0c00945,10.1038/s41929-019-0392-6,10.1002/adsc.201901398,10.1021/acs.orglett.9b03189,10.1021/acs.orglett.9b02577,10.1002/adsc.201801707,10.1021/jacs.9b03280,10.1002/anie.201814572,10.1055/s-0037-1611659,10.1038/s41467-019-08631-1,10.1016/j.apsusc.2018.09.154,10.6023/cjoc201809037,10.1002/anie.201810757,10.1021/jacs.8b10874,10.1002/ajoc.201800535,10.1021/jacs.8b09401,10.1021/acs.joc.8b02279,10.1039/c8cc07093h,10.1055/s-0037-1610161,10.1021/jacs.8b06966,10.1021/jacs.8b05374,10.1021/jacs.8b03163,10.1002/ejoc.201800330,10.1021/acs.orglett.8b01268,10.1021/acs.orglett.8b00583,10.1039/c7nj04701k,10.1021/acs.orglett.7b03713,10.1039/c7sc04351a,10.1039/c7nj02997g,10.1021/acs.orglett.7b03289,10.1002/anie.201710241,10.1002/anie.201707134,10.1002/anie.201706719,10.1021/jacs.7b06340,10.1002/aoc.3677,10.1039/c7sc01204g,10.1021/jacs.7b02742,10.1021/jacs.7b00643,10.1002/ejoc.201601253,10.1021/acscatal.6b03277,10.1007/s10562-016-1880-9,10.1002/chem.201602939,10.1021/acscatal.6b01816,10.1039/c6cc08182g,10.1039/c6ob02269c,10.1039/c6ra02989b,10.1039/c6ra01918h,10.1039/c5cy02235e,10.1039/c6cc03835b,10.1021/acs.joc.5b02557,10.1002/anie.201507776,10.1016/j.tet.2015.08.023,10.1021/acs.orglett.5b02482,10.1055/s-0035-1560457,10.1016/j.jorganchem.2014.12.033,10.1021/acscatal.5b01075,10.1080/00268976.2015.1023751,10.1021/jacs.5b05597,10.1002/ajoc.201500148,10.1021/acs.accounts.5b00064,10.1002/anie.201409617,10.1039/c5cc02254a,10.1039/c5cc05312a,10.1039/c5ob00515a,10.1021/ol502207z,10.1002/adsc.201400548,10.1016/j.tet.2014.03.039,10.1021/ja5026485,10.1002/anie.201402893,10.1038/nature13274,10.1016/j.catcom.2014.01.022,10.1002/anie.201305972,10.1002/anie.201308391,10.1002/cctc.201300903,10.1039/c4ra08421g,10.1039/c4ob00813h,10.1039/c4cc02923b,10.1039/c4cc00867g,10.1039/c4cc00297k,10.1039/c4ra01153h,10.1055/s-0033-1340061,10.1002/chem.201303668,10.1002/chem.201302962,10.1016/j.tetlet.2013.08.136,10.1021/ja409661n,10.1002/anie.201303916,10.2174/1389557511313060003,10.1002/chem.201203694,10.1016/j.comptc.2012.10.025,10.1021/ja311045f,10.1021/ja3116718,10.3762/bjoc.9.6,10.1021/ja3089422,10.1039/c3dt51087e,10.1351/PAC-CON-12-09-14,10.1021/ol3028913,10.1002/adsc.201200624,10.1021/ja307371w,10.1016/j.ica.2012.04.037,10.1021/ja304099j,10.1021/ja304344h,10.1021/ja2084509,10.1002/anie.201108350,10.1002/anie.2012018063/11/2022NOV 302011FALSEFALSEFALSEFALSE1334719020
16
18FALSEanie.20090704010.1002/anie.200907040https://sci-hub.wf/10.1002/anie.200907040https://doi.org/10.1002/anie.200907040NiC-H ActivationLongTRUE1609722010Hu, XL
The Nickel/Copper-Catalyzed Direct Alkylation of Heterocyclic C-H Bonds
ANGEW CHEM INT EDIT
Ecole Polytech Fed Lausanne
4/1/2010FALSEFALSEFALSECsp2_ar-Csp3E-NuHXHClHetAlkylIonic-OtBuNu-H_10.1002/anie.201510743,10.1002/anie.201309584,10.1002/adsc.201100487,10.1002/chem.201001631,10.1021/acscatal.6b02003,10.1021/ja413131m,10.1021/ja401344e,10.1021/acs.organomet.6b00201,10.1039/c2cc32396f10.1021/acs.orglett.1c02575,10.1039/d0cs01441a,10.1039/d1cc02885e,10.1016/j.tet.2021.132152,10.1002/chem.202100475,10.1002/tcr.202100113,10.1039/d1nj01698a,10.1039/d1ra01522b,10.1021/acscatal.0c05580,10.3390/molecules25214970,10.1002/anie.202009527,10.1021/acs.organomet.0c00161,10.1016/j.chempr.2020.04.005,10.1021/acs.joc.0c00141,10.1002/adsc.201901670,10.1002/adsc.201901078,10.1016/j.tet.2019.05.047,10.1002/chem.201900822,10.1016/j.tetlet.2019.06.005,10.1021/acs.organomet.9b00060,10.1002/anie.201806631,10.1080/10426507.2019.1602626,10.1039/c8gc03895c,10.1007/s10593-019-02442-4,10.1021/acscatal.8b04872,10.1021/acs.chemrev.8b00507,10.1016/j.tet.2018.12.013,10.1021/acs.orglett.8b03924,10.3866/PKU.WHXB201809036,10.1039/c8dt03210f,10.1021/acscatal.8b03770,10.1021/acs.orglett.8b02699,10.1055/s-0036-1592000,10.1002/anie.201801982,10.1021/acs.organomet.8b00025,10.5059/yukigoseikyokaishi.75.1133,10.1007/s12039-017-1338-7,10.1021/acs.orglett.7b01775,10.1039/c7ob01232b,10.1021/acs.organomet.7b00129,10.1039/c6sc05622a,10.1021/acs.orglett.6b03287,10.1021/acs.joc.6b02211,10.1021/acscatal.6b02477,10.1021/acscatal.6b01956,10.1002/cctc.201600606,10.1002/anie.201604696,10.1038/537156a,10.1021/acscatal.6b02003,10.1021/acs.orglett.6b01675,10.1007/s41061-016-0053-z,10.1002/adsc.201600590,10.1002/chem.201601482,10.1021/acs.organomet.6b00201,10.1021/acs.organomet.6b00008,10.1002/anie.201510743,10.1021/jacs.6b00250,10.1021/acs.joc.5b02433,10.1016/bs.adomc.2016.07.001,10.1007/3418_2015_114,10.1021/acscatal.5b02324,10.1002/chem.201503809,10.1002/anie.201507829,10.1021/jacs.5b07507,10.1002/anie.201504735,10.1021/jacs.5b02435,10.1246/cl.150024,10.1021/jacs.5b01365,10.1002/chem.201406562,10.1016/j.tetlet.2014.12.029,10.1021/ja511557h,10.1021/jo5025317,10.1039/c5dt00032g,10.1039/c5cc02254a,10.1039/c4ob02488e,10.1070/RCR4525,10.1002/cplu.201402169,10.1002/anie.201408355,10.1016/j.tet.2014.08.049,10.1002/anie.201407848,10.1021/ol502314p,10.1016/j.tet.2014.07.022,10.1016/j.ccr.2014.06.016,10.1002/chem.201403246,10.1016/j.jorganchem.2014.02.013,10.1515/pac-2014-5032,10.1002/anie.201309584,10.1021/ja412107b,10.1021/ja413131m,10.1055/s-0033-1340068,10.1021/ol403021p,10.1002/ejoc.201301441,10.1021/ol4027073,10.1055/s-0033-1338544,10.1021/ja407589e,10.1021/ol402494e,10.1021/ol402644y,10.1021/ja406484v,10.1002/chem.201301409,10.1021/ja401466y,10.1021/ja401344e,10.1021/ja312277g,10.3184/174751913X13575704209748,10.1002/chem.201203413,10.1016/B978-0-12-404598-9.00001-8,10.1002/anie.201209312,10.1002/anie.201208203,10.1039/c3cc43915a,10.1039/c3sc51747k,10.1016/j.tetlet.2012.09.131,10.1055/s-0032-1317035,10.1002/adsc.201200345,10.1021/ol300570f,10.1021/ol300348w,10.1021/om201279j,10.1016/j.tet.2011.12.072,10.1021/ol203175a,10.1021/om2007612,10.1007/128_2011_288,10.1039/c2cc35758e,10.1039/c2cc32396f,10.2533/chimia.2012.154,10.1039/c2cc18156h,10.1002/anie.201106825,10.1002/anie.201200809,10.1039/c2cc30429e,10.1002/adsc.201100487,10.1021/ol201779n,10.1021/ja206850s,10.1021/ol201930e,10.1016/j.tet.2011.06.044,10.1021/jo200452x,10.1021/ol200366n,10.1021/ja111249p,10.1021/cr100327p,10.1055/s-0030-1259332,10.1002/anie.201104735,10.1002/anie.201105964,10.1039/c1cc13086b,10.1039/c1cc14718h,10.1039/c1sc00368b,10.2533/chimia.2011.646,10.1039/c1dt10195a,10.1002/ejoc.201000928,10.1021/jo101433g,10.1021/ol101684u,10.1021/ol101777x,10.1021/om1007506,10.1021/ci100209a,10.1021/ol101450u,10.1002/anie.201003895,10.1039/c0cc00778a,10.1002/chem.201001631,10.2533/chimia.2010.231,10.1039/c0ob00212g3/11/20222010FALSEFALSEFALSEFALSE49173061
17
19FALSEacscatal.7b0044210.1021/acscatal.7b00442https://sci-hub.wf/10.1021/acscatal.7b00442https://doi.org/10.1021/acscatal.7b00442NiC-N ActivationGerry20-FebTRUE2933552017Ohshima, T
Direct Catalytic Alcoholysis of Unactivated 8‑Aminoquinoline AmidesACS Catal.
Direct catalytic alcoholysis of unactivated amides is one of the most difficult challenges in organic chemistry, and an applicable method for cleaving amides used as directing groups in regioselective functionalization reactions has not been reported. Herein, we report direct catalytic alcoholysis of 8-aminoquinoline amides, which are highly effective directing groups in regioselective functionalization reactions. The reactions proceeded with a simple combination of substrates, air-stable catalysts, and alcohols, affording the corresponding esters in good yields with broad functional group tolerance. Highly chemoselective cleavage of the 8-aminoquinoline amides in the presence of related Carbonyl functionalities and preliminary mechanistic studies are also described.
3/28/2017Csp2-Csp3E-NuNO
8-aminoquinoline
OH
Carbonyl
AlkylNo baseNo Base_10.1021/acscatal.7b03688,10.1002/chem.201702867,10.1021/acs.orglett.8b0102110.1021/acscatal.1c05738,10.1002/ajoc.202100736,10.1021/acs.joc.1c02245,10.1021/acs.joc.1c02245,10.1021/acs.chemrev.1c00519,10.1016/j.cclet.2021.01.034,10.1002/tcr.202100117,10.1021/acscatal.1c00625,10.1002/chem.202100093,10.1039/d0cy02230f,10.1002/cjoc.202000500,10.1039/d0ob02232b,10.1016/j.mcat.2020.111318,10.1038/s41467-020-20182-4,10.1021/acs.orglett.0c03416,10.1021/acscatal.0c03334,10.1002/adsc.202000730,10.1021/acs.joc.0c01458,10.1021/acs.orglett.0c02457,10.1002/chem.202001447,10.1021/acs.orglett.0c00885,10.1016/j.chempr.2019.12.026,10.1007/s10562-019-02966-6,10.1007/s11426-019-9665-5,10.1021/acs.chemrev.9b00495,10.1021/acscatal.9b04285,10.1021/acs.orglett.9b03434,10.3987/COM-19-S(F)30,10.1039/c9cc07466j,10.1021/acs.orglett.9b03274,10.1021/acs.joc.9b01362,10.1021/acs.joc.9b02299,10.1002/anie.201910304,10.1039/c9sc03440d,10.1002/tcr.201900044,10.1039/c9cc05321b,10.1021/acs.orglett.9b02109,10.1002/chem.201900543,10.1002/anie.201808159,10.1021/acs.oprd.8b00424,10.1021/acscatal.9b00181,10.3390/molecules24071234,10.1002/anie.201814272,10.1039/c8sc05819a,10.1021/acscatal.8b04654,10.1021/acs.organomet.8b00684,10.1002/cctc.201801098,10.1002/asia.201801317,10.1021/acscatal.8b04516,10.1021/acs.joc.8b02451,10.1039/c8cs00201k,10.1002/anie.201807664,10.1021/acs.orglett.8b01440,10.1039/c8sc01735b,10.1021/acs.orglett.8b01021,10.1021/acs.joc.8b00160,10.1021/jacs.8b02124,10.1021/acs.joc.8b00174,10.1021/jacs.8b00641,10.1021/acscatal.7b03688,10.1021/acscatal.7b02599,10.1039/c7ra12152k,10.1002/chem.201702867,10.1039/c7sc01750b,10.1021/acs.orglett.7b011942/23/2022
18
20FALSEacscatal.8b0187910.1021/acscatal.8b01879https://sci-hub.wf/10.1021/acscatal.8b01879https://doi.org/10.1021/acscatal.8b01879NiDeletedGerry21-FebFALSE468382018
Stradiotto, M
#N/ABisphosphines: A Prominent Ancillary Ligand Class for Application in Nickel-Catalyzed C-N Cross-CouplingACS Catal.
The Ni-catalyzed Csp2–N cross-coupling of NH substrates and (hetero)aryl (pseudo)halides for the synthesis of (hetero)anilines is in the midst of a resurgence. Reactivity breakthroughs that have been achieved in this field within the past five years have served to establish Ni catalysis as being competitive with, and in some cases superior to, more well-established Pd- or Cu-based protocols. Whereas the repurposing of useful ancillary ligands from the Pd domain has been the most frequently employed approach in the quest to develop effective Ni-based catalysts for such transformations, considerable progress has been made as of late in the design of ancillary ligands tailored specifically for use with Ni. Bisphosphine ancillary ligands have proven to be well-suited for such an approach, given their modular and facile syntheses; several variants have emerged recently that are particularly effective in enabling a range of otherwise challenging Ni-catalyzed Csp2–N cross-couplings. This Perspective presents a comprehensive summary of the advancements within the field of Ni-catalyzed Csp2–N cross-coupling through the application of the bisphosphine ancillary ligand class. It is our intention that the discussion of key ancillary ligand design concepts and mechanistic considerations presented herein will provide a useful platform for researchers to initiate ancillary ligand design efforts for the development of high-performing Ni cross-coupling catalysts.
8/1/2018_10.1002/anie.202002392,10.1021/acscatal.9b00884,10.1002/anie.202014340,10.1126/science.abj4213,10.1021/acscatal.1c03010,10.1002/anie.202200352,10.1039/c9cc07840a,10.1021/jacs.0c0028610.1002/anie.202200352,10.1021/acs.oprd.1c00410,10.1021/acscatal.1c04705,10.1021/acscatal.1c05386,10.1002/slct.202103723,10.1021/jacs.1c12622,10.1021/acscatal.1c05386,10.1021/acscatal.1c04705,10.1021/acs.oprd.1c00410,10.1021/acs.orglett.1c03541,10.1002/chem.202103341,10.2533/chimia.2021.943,10.1126/science.abj4213,10.1021/acscatal.1c03010,10.1021/acs.organomet.1c00369,10.1080/00958972.2021.1955251,10.1002/anie.202103803,10.1039/d1cy00660f,10.1002/ejoc.202100194,10.1016/j.tetlet.2021.153001,10.1039/d1ob00080b,10.1039/d0cc08389e,10.1021/acs.orglett.0c04056,10.1002/anie.202012877,10.1016/bs.adomc.2021.04.003,10.1002/anie.202014340,10.1021/acscatal.0c04280,10.1055/a-1337-6459,10.1021/jacs.0c07381,10.1002/cplu.202000606,10.1021/acs.orglett.0c02672,10.1021/acs.orglett.0c02909,10.1021/acscatal.0c02514,10.1021/jacs.0c05901,10.1002/chem.202002800,10.1021/jacs.0c06139,10.1021/acscatal.0c02683,10.1039/d0dt02063j,10.1016/j.mcat.2020.110915,10.1021/acscatal.0c01414,10.1021/acs.joc.0c00139,10.1039/d0sc01084g,10.1021/jacs.9b13531,10.1002/anie.202002392,10.1021/jacs.0c00286,10.3390/molecules25051141,10.1039/d0re00036a,10.1039/c9cc07840a,10.1002/anie.201910436,10.1021/acs.orglett.9b02990,10.1039/c9cc05707b,10.1021/acs.organomet.9b00453,10.1002/ejic.201900972,10.1039/c9qo00726a,10.1002/anie.201904795,10.1021/acs.organomet.9b00543,10.1039/c9cc04634h,10.1002/adsc.201900545,10.1021/acs.oprd.9b00226,10.1021/acs.orglett.9b01968,10.1055/s-0037-1611852,10.1021/acs.chemrev.8b00588,10.1002/anie.201900095,10.1021/acscatal.9b00884,10.1002/adsc.201801661,10.1016/j.poly.2019.01.021,10.1002/slct.201803770,10.1002/anie.201812862,10.1021/acs.organomet.8b00451,10.1021/acs.joc.8b02588,10.1021/acs.organomet.8b00589,10.1021/acs.organomet.8b00605Kelly#N/A
19
225FALSEanie.20080381410.1002/anie.200803814https://sci-hub.wf/10.1002/anie.200803814https://doi.org/10.1002/anie.200803814NiC-O ActivationShihongTRUE15640282008Shi, ZJ
Cross-Coupling of Aryl/Alkenyl Pivalates with Organozinc Reagents through Nickel-Catalyzed C-O Bond Activation under Mild Reaction Conditions
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Chinese Acad Sci12/12/2008German version of exist articleCsp2_ar-Csp2_arE-NuOZnOPivZnXArylArylNo baseNo BaseMedium0.33_10.1021/ja200398c,10.1021/ja210249h,10.1021/ol9029534,10.1021/ol9028308,10.1002/anie.202114556,10.1002/anie.201100683,10.1002/chem.200902785,10.1021/acscatal.6b00801,10.1038/s41929-020-00560-3,10.1021/ja810157e,10.1021/ol401727y,10.1021/acscatal.7b01058,10.1002/chem.201602202,10.1021/ol4011757,10.1021/ja903091g,10.1002/anie.200907287,10.1002/chem.201103050,10.1021/acscatal.7b00941,10.1021/ol901978e,10.1021/acs.orglett.6b02656,10.1246/cl.2011.913,10.1002/anie.200900329,10.1016/j.tet.2012.04.005,10.1021/acs.joc.6b01627,10.1021/acscatal.9b00744,10.1002/chem.201103784,10.1021/ja2084509,10.1021/jacs.1c09797,10.1002/anie.201412051,10.1039/c4qo00321g,10.1021/om300566m,10.1002/chem.201003731,10.1021/acs.orglett.6b01398,10.1039/c1cc16582h,10.1021/acs.orglett.7b00556,10.1002/anie.200907359,10.1021/om500452c,10.1002/anie.201806790,10.1039/c1sc00230a,10.1021/acs.joc.8b0249810.1039/d1ob02051j,10.1021/acscatal.1c00247,10.1177/17475198211063806,10.1002/anie.202114556,10.1021/acs.joc.1c00204,10.1021/jacs.1c09797,10.1002/aoc.6430,10.1039/d1ob00955a,10.1039/c9cs00571d,10.1002/chem.202101101,10.1002/anie.202103465,10.1021/acs.organomet.1c00085,10.1039/d0cc08389e,10.1002/ajoc.202100031,10.1038/s41929-020-00560-3,10.1021/acs.joc.0c02389,10.1055/a-1349-3543,10.1055/a-1306-3228,10.1021/acs.joc.0c02266,10.1002/cjoc.202000319,10.1021/acs.chemrev.0c00088,10.1002/anie.202006586,10.1021/acs.orglett.0c01937,10.1039/d0sc01585g,10.1021/acs.organomet.0c00338,10.1021/acs.orglett.0c01127,10.1002/cjoc.201900506,10.1134/S1070363219120405,10.1021/jacs.9b08586,10.1021/acs.joc.9b01556,10.1016/j.jcat.2019.07.026,10.1039/c9qo00536f,10.1080/10426507.2018.1543305,10.1002/cjoc.201800575,10.1021/acscatal.9b00744,10.1021/acs.organomet.8b00720,10.1007/3418_2018_19,10.1021/acs.accounts.8b00408,10.1016/j.tet.2018.10.025,10.1021/acs.joc.8b02498,10.1002/adsc.201800729,10.1002/anie.201805486,10.1002/anie.201806790,10.1021/acs.orglett.8b00775,10.1021/acs.orglett.8b00674,10.1021/acs.orglett.7b03713,10.1039/c7ob02947k,10.1039/c7cc08709h,10.1021/acs.orglett.7b03669,10.1021/acs.joc.7b02588,10.1039/c7nj02488f,10.1021/acscatal.7b00941,10.1039/c7qo00068e,10.1021/acscatal.7b01058,10.1021/acs.orglett.7b00447,10.1021/acs.orglett.7b00556,10.1002/anie.201611720,10.1021/acscatal.7b00245,10.1021/jacs.6b12329,10.1021/acscatal.6b02964,10.1021/acs.orglett.6b02656,10.1246/cl.160712,10.1021/acs.joc.6b01627,10.1021/acscatal.6b01956,10.1002/chem.201602150,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1002/chem.201602202,10.1021/acscatal.6b00801,10.1021/acs.orglett.6b01398,10.1016/j.tet.2016.03.074,10.1016/j.tet.2016.02.069,10.1016/bs.adomc.2016.07.001,10.1039/c5cc10005d,10.1002/ejoc.201500987,10.1002/anie.201504524,10.1002/ejoc.201500630,10.1021/acs.orglett.5b01229,10.1002/adsc.201500304,10.1016/j.tet.2015.02.088,10.1002/anie.201412051,10.1021/ar500345f,10.1021/ja512498u,10.1039/c4qo00321g,10.1039/c5cc01378j,10.1021/ol502499q,10.1021/om500452c,10.1038/nature13274,10.1002/chem.201303809,10.1515/pac-2014-5038,10.1016/j.inoche.2013.12.026,10.1021/ja412107b,10.1021/ja410883p,10.1039/c4dt02374a,10.1039/c3dt52412d,10.1002/anie.201304884,10.1021/ol401727y,10.1021/ol4011757,10.1021/jp312690e,10.1002/ejoc.201300197,10.1021/ja312464b,10.1016/j.tet.2013.01.053,10.1007/3418_2012_42,10.1021/op300236f,10.1002/adsc.201200364,10.1021/om300566m,10.1016/j.tet.2012.04.005,10.1002/adsc.201200369,10.1002/chem.201103784,10.1021/ja210249h,10.1021/ja2084509,10.1002/anie.201202466,10.1002/chem.201103050,10.1002/anie.201203778,10.1039/c1cc16582h,10.1021/ja207759e,10.1021/ja2059999,10.1246/cl.2011.913,10.1246/cl.2011.1001,10.1002/adsc.201000975,10.1021/ja200398c,10.1002/chem.201003731,10.1021/jo102417x,10.1021/cr100259t,10.1002/anie.201100683,10.1002/anie.201103599,10.1039/c1sc00230a,10.1021/ja106943q,10.1021/ar100082d,10.1002/adsc.201000311,10.1055/s-0030-1258116,10.1021/ja1033167,10.1016/j.tetlet.2010.03.110,10.1002/adsc.201000144,10.1021/ol9029534,10.1021/ol9028308,10.1002/anie.200907287,10.1002/anie.200907359,10.1002/chem.200902785,10.1021/om900771v,10.1055/s-0029-1218283,10.1055/s-0029-1217032,10.1021/ol901978e,10.1021/ja907281f,10.1002/adsc.200900375,10.1021/om900558a,10.1021/ja903091g,10.1021/ja810157e,10.1002/anie.200900329,10.1002/anie.200903146Kelly11/4/2021
20
23FALSEs41467-021-25222-110.1038/s41467-021-25222-1https://sci-hub.wf/10.1038/s41467-021-25222-1https://doi.org/10.1038/s41467-021-25222-1NiC-N ActivationKellyTRUE41#N/A2021
Zhang, XJ; Zhang, GS
Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN2 pincer ligandNAT COMMUN
Alkynes are amongst the most valuable functional groups in organic chemistry and widely used in chemical biology, pharmacy, and materials science. However, the preparation of alkyl-substituted alkynes still remains elusive. Here, we show a nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts. Key to the success of this coupling is the development of an easily accessible and bench-stable amide-type pincer ligand. This ligand allows naturally abundant alkyl amines as alkylating agents in Sonogashira reactions, and produces diverse alkynes in excellent yields under mild conditions. Salient merits of this chemistry include broad substrate scope and functional group tolerance, gram-scale synthesis, one-pot transformation, versatile late-stage derivatizations as well as the use of inexpensive pre-catalyst and readily available substrates. The high efficiency and strong practicability bode well for the widespread applications of this strategy in constructing functional molecules, materials, and fine chemicals. Alkynes are amongst the most valuable functional groups in organic chemistry, however, the preparation of alkyl-substituted alkynes still remains elusive. Here the authors show a nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts.
Henan Normal Univ8/12/2021TRUETRUEFALSEyCsp3-Csp3E-NuNH
Triphenylpyridinium+BF4-
HAlkylAlkylK3PO4Ionic-PO4Unique_xx
Added by Imanuel
10.1039/d2gc00395c,10.1055/s-0040-1719881
Long11/10/2021
21
187FALSEanie.20090032910.1002/anie.200900329https://sci-hub.wf/10.1002/anie.200900329https://doi.org/10.1002/anie.200900329NiC-O ActivationKellyTRUE9621702009Goossen, LJ
C(aryl)-O Activation of Aryl Carboxylates in Nickel-Catalyzed Biaryl Syntheses
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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Nickel-Catalyzed Amination of Aryl Pivalates by the Cleavage of Aryl C-O Bonds
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Osaka Univ3/30/2010TRUEFALSEFALSECsp2_ar-Nsp3E-NuOHOPivHAryl
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Direct Application of Phenolic Salts to Nickel-Catalyzed Cross-Coupling Reactions with Aryl Grignard Reagents
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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Nickel-Catalyzed Amination of Aryl Sulfamates
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Univ Calif Los Angeles
1/20/2011FALSEFALSEFALSECsp2_ar-Nsp3E-NuOH
OSO2NMe2
HAryl
Morpholine
NaOtBuIonic-OtBuWeak0.36_10.1021/ol200267b,10.1021/ja200398c,10.1021/acscatal.6b00865,10.1021/jacs.7b04973,10.1002/chem.201605095,10.1039/c8qo00764k,10.1021/ja210249h,10.1021/acs.orglett.7b00556,10.1021/acscatal.8b01879,10.1039/c4qo00321g,10.1002/anie.201410875,10.1021/ol401727y,10.1039/c1sc00230a,10.1021/ol203322v,10.1021/ol201437g,10.1021/cs501045v,10.1021/acscatal.7b02817,10.1021/acscatal.6b00801,10.1021/jacs.9b02751,10.1021/ol301847m,10.1021/ja5029793,10.1021/ol403209k,10.1021/om500452c10.1002/anie.202108587,10.1055/a-1548-8362,10.1021/acs.orglett.1c00855,10.1039/d0nj05711h,10.1002/anie.202012877,10.1002/adsc.202001262,10.1021/acscatal.0c03334,10.1021/acs.orglett.0c02909,10.1021/acs.chemrev.0c00088,10.1039/d0gc02404j,10.1002/chem.202002800,10.1039/d0nj01610a,10.1039/d0sc01585g,10.1021/acs.organomet.0c00338,10.1007/s41061-020-0300-1,10.1016/j.jpcs.2019.109256,10.1021/acs.orglett.9b04119,10.1002/chem.201904288,10.1021/acscatal.9b02636,10.1021/acs.orglett.9b02621,10.1055/s-0037-1611732,10.1039/c9dt00455f,10.1039/c9ob00817a,10.1002/anie.201901814,10.1021/jacs.9b02751,10.20964/2019.04.38,10.1021/acs.orglett.9b00294,10.1021/jacs.8b12495,10.1021/acs.organomet.8b00720,10.3906/kim-1811-6,10.1002/cctc.201801350,10.1039/c8qo00764k,10.1016/j.tetlet.2018.08.015,10.1039/c8cc05437a,10.1021/acscatal.8b01879,10.3390/molecules23071715,10.1021/jacs.8b03744,10.1021/acs.joc.8b00592,10.1016/j.jorganchem.2018.01.019,10.1021/acscatal.8b00856,10.1002/aoc.4273,10.1021/acs.orglett.8b00060,10.1039/c7cc08709h,10.1021/acscatal.7b03215,10.1002/aoc.3855,10.1021/acscatal.7b02817,10.1039/c7gc02804k,10.1002/anie.201706982,10.1021/jacs.7b04973,10.1039/c7ob01791j,10.1055/s-0036-1590819,10.1021/acs.orglett.7b01549,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1002/adsc.201601105,10.1016/j.tet.2017.01.050,10.1021/acscatal.6b03543,10.1016/j.jorganchem.2016.12.029,10.1021/acscatal.6b03277,10.1021/acscatal.6b02964,10.1002/chem.201605095,10.1021/acs.chemrev.6b00237,10.1002/anie.201606979,10.1021/acs.orglett.6b01758,10.1002/tcr.201500305,10.1021/acscatal.6b00801,10.1021/acscatal.6b00865,10.1016/j.tet.2016.03.005,10.1021/acscatal.5b02021,10.1039/c6ob00073h,10.1039/c6ra14367a,10.1021/acs.oprd.5b00314,10.1002/ejoc.201500987,10.1002/ejoc.201500734,10.1002/ejoc.201500630,10.1021/acs.joc.5b01272,10.1021/acs.orglett.5b01229,10.1002/ejoc.201500226,10.1002/anie.201500404,10.1002/anie.201410875,10.1021/ed500158p,10.1016/j.molcata.2014.10.031,10.1039/c4qo00321g,10.1039/c4ob01627k,10.1039/c4cc06445c,10.1021/ja5099935,10.1021/om500452c,10.1021/ol5024344,10.1021/cs501045v,10.1002/anie.201404355,10.1002/adsc.201400201,10.1021/ja5029793,10.1021/cr400230c,10.1021/jo402723e,10.1021/ja4118413,10.1021/ja411911s,10.1021/ol403209k,10.1039/c3ob42053a,10.1039/c3ob41382a,10.1595/147106713X672311,10.1021/ol401727y,10.1021/ol4007162,10.1016/j.jfluchem.2012.12.001,10.1021/ol303130j,10.1038/NCHEM.1504,10.1021/op300236f,10.1016/j.tetlet.2012.08.015,10.1021/ol301847m,10.1002/chem.201201394,10.1016/j.tetlet.2012.05.081,10.1021/ol301681z,10.1021/ol3002442,10.1002/chem.201103882,10.1021/ol203322v,10.1021/ja210249h,10.1002/anie.201202466,10.1039/c2ob25425e,10.1002/anie.201202136,10.1021/ar200055y,10.1021/ol201437g,10.1021/ja200398c,10.1021/ol200267b,10.1039/c1cc15503b,10.1039/c1sc00230aKelly11/22/20212011FALSEFALSEFALSEFALSE5092171
25
159FALSEanie.20110119110.1002/anie.201101191https://sci-hub.wf/10.1002/anie.201101191https://doi.org/10.1002/anie.201101191NiC-O ActivationLong17-FebTRUE899452011Doyle, AG
Nickel-Catalyzed Cross-Coupling of Styrenyl Epoxides with Boronic Acids
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Princeton Univ5/13/2011Csp3-Csp2_arE-NuOB
O(Ring-Opening)
B(OH)2AlkylArylK3PO4Ionic-PO4Weak1TM10.1021/ja410704d,10.1021/ol300364s,10.1039/c9cc08079a,10.1021/jo300547v,10.1021/ja3013825,10.1126/science.abj4213,10.1038/NCHEM.2741,10.1021/jacs.5b01909,10.1021/ja507642610.1039/d2cc00461e,10.1021/jacs.1c11170,10.1016/j.chempr.2021.10.023,10.1002/ejoc.202101211,10.6023/cjoc202106021,10.1126/science.abj4213,10.1016/j.tetlet.2021.153369,10.1021/jacs.1c08105,10.1016/j.poly.2021.115363,10.1039/c9cs00571d,10.1021/jacs.1c00659,10.1039/d1ob00259g,10.1002/adsc.202001493,10.1002/anie.202015021,10.1039/d0qo01016b,10.1021/acs.orglett.0c02478,10.1039/d0ob01226b,10.1021/acs.joc.0c00899,10.1021/acscatal.0c01199,10.1039/c9cc10089j,10.1002/jhet.3918,10.1021/acs.orglett.0c00061,10.1039/c9cc08079a,10.1016/j.trechm.2019.08.004,10.1039/c9fd00041k,10.1016/j.tetlet.2019.151216,10.1039/c9dt03201k,10.1021/acs.orglett.9b01782,10.1039/c9qo00352e,10.1021/jacs.9b04993,10.1039/c9cc02956g,10.6023/cjoc201811035,10.1002/chem.201805987,10.1021/jacs.8b11752,10.6023/cjoc201803001,10.1039/c8qo00091c,10.1039/c7sc04351a,10.1002/slct.201702416,10.1039/c7ob01793f,10.1021/acs.orglett.7b01858,10.1002/chem.201702824,10.1021/acs.orglett.7b02076,10.1002/chem.201702200,10.1038/NCHEM.2741,10.1021/jacs.7b00643,10.1021/acs.orglett.6b03430,10.1039/c6cs00150e,10.1021/acs.inorgchem.6b01218,10.1055/s-0035-1561602,10.1002/adsc.201501015,10.1002/chem.201504959,10.1039/c6ob01171c,10.1039/c5cc09817c,10.1039/c6cc04410g,10.1021/jacs.5b06735,10.1002/ejoc.201500734,10.1055/s-0034-1380141,10.1021/jacs.5b01909,10.1039/c4cc09321f,10.1016/S1872-2067(14)60217-5,10.1002/anie.201407083,10.1021/ol503004a,10.1021/ja5076426,10.1002/adsc.201400560,10.1021/cr500036t,10.1055/s-0033-1339032,10.1002/adsc.201400201,10.1002/anie.201310193,10.1021/ja410704d,10.1039/c3cc47360k,10.1021/ja4076716,10.1002/ejoc.201300558,10.1021/om400424a,10.1021/ja400325w,10.1021/ol400444g,10.1039/c3dt51562a,10.1021/ja310351e,10.1021/jo300547v,10.1021/ja3013825,10.1002/chem.201103882,10.1021/ol300364s,10.1021/ja208461k,10.1021/ja205174cKelly1/6/2022
26
29FALSEjacs.1c0661410.1021/jacs.1c06614https://sci-hub.wf/10.1021/jacs.1c06614https://doi.org/10.1021/jacs.1c06614NiC-H ActivationGerryTRUE51#N/A2021Shi, SL
Enantioconvergent Arylation of Racemic Secondary Alcohols to Chiral Tertiary Alcohols Enabled by Nickel/N-Heterocyclic Carbene Catalysis
J AM CHEM SOC
The direct upgrading reaction of simple and readily available achiral alcohols via C-H functionalization is an ideal strategy to prepare value-added chiral higher alcohols. Herein, we disclose the first enantioconvergent upgrading reaction of simple racemic secondary alcohols to enantioenriched tertiary alcohols. An N-heterocyclic carbene (NHC)-nickel catalyst was leveraged to enable this highly efficient formal asymmetric alcohol alpha-C-H arylation via a dehydrogenation using phenyl triflate as a mild oxidant followed by asymmetric addition of arylboronic esters to the transient ketones. Mechanistic studies and control experiments were conducted to reveal the possible reasons for the exceptional control over chemo- and enantioselectivity.
Univ Chinese Acad Sci
8/11/2021TRUEFALSEFALSEyCsp3-Csp2_arNu-NuHHHHAlkylArylNaOMeIonic-ORNu-H_xx10.1021/acscatal.1c0520810.1021/jacs.1c12625,10.1002/ajoc.202100723,10.1039/d1dt02951g11/15/2021AUG 112021FALSEFALSEFALSEFALSE1433111963
27
30FALSEacscatal.1c0162610.1021/acscatal.1c01626https://sci-hub.wf/10.1021/acscatal.1c01626https://doi.org/10.1021/acscatal.1c01626NiC-H ActivationLongTRUE111552021Mashima, K
Mechanistic Study of Ni and Cu Dual Catalyst for Asymmetric C-C Bond Formation; Asymmetric Coupling of 1,3-Dienes with C-nucleophiles to Construct Vicinal StereocentersACS CATAL
We report details of the reaction mechanism for a coupling reaction of 1,3-dienes with C-nucleophiles that was catalyzed by a Ni/Cu cooperative catalyst system using Ni(cod)(2) and [Cu(CH3CN)(4)]PF6 in the presence of a chiral JOSIPHOS-type bisphosphine ligand and (Pr2NEt)-Pr-i, providing direct access to highly valuable vicinal quaternary and tertiary stereocenters with high enantio- and diastereoselectivity. The bimetallic cooperative catalyst system exhibited a broad substrate scope, including both cyclic/acyclic stabilized nucleophiles and aryl-/alkyl-substituted 1,3-dienes. The bimetallic cooperative catalyst mechanism was elucidated in depth by isolating and characterizing four key complexes of nickel and copper and conducting deuterium labeling experiments, kinetic studies, and density functional theory calculations. The turnover-limiting step of this reaction is the proton-transfer step to diene-coordinated Ni complex 6 from cationic Cu complex 8 to yield p-allyl Ni complex 7 and Cu enolate complex 9, respectively. The stereoselectivity of the reaction was also clarified according to single-point calculations of the key intermediates 7 and 9.
Osaka Univ6/4/2021TRUETRUETRUEyyCsp2-Csp3Nu-NuHHHHVinylAlkylDIPEANitrogenNitrogen(neutral)Nu-H_xx10.1021/acscatal.1c0480010.1039/d1qo01927a,10.1021/jacs.1c12664,10.1021/acscatal.1c05517,10.1021/acscatal.1c04800,10.1002/anie.202112390,10.1002/anie.202111842,10.1038/s41467-021-25981-x11/1/2021JUN 42021FALSEFALSEFALSEFALSE11116643
28
31FALSEjacs.1c0389810.1021/jacs.1c03898https://sci-hub.wf/10.1021/jacs.1c03898https://doi.org/10.1021/jacs.1c03898NiDeletedFALSE421272021Watson, MP#N/AOvercoming the Naphthyl Requirement in Stereospecific Cross-Couplings to Form Quaternary Stereocenters
J AM CHEM SOC
The use of a simple stilbene ligand has enabled a stereospecific Suzuki-Miyaura cross-coupling of tertiary benzylic carboxylates, including those lacking naphthyl substituents. This method installs challenging all-carbon diaryl quaternary stereocenters in good yield and ee and represents an important breakthrough in the naphthyl requirement that pervades stereospecific cross-couplings involving enantioenriched electrophiles.
Univ Delaware6/16/2021_10.1021/acs.oprd.1c00410,10.1021/acs.oprd.1c00410,10.6023/cjoc202106021,10.1002/adma.202105196,10.1002/tcr.202100210#N/A
29
216FALSEanie.20110146110.1002/anie.201101461https://sci-hub.wf/10.1002/anie.201101461https://doi.org/10.1002/anie.201101461NiC-O ActivationLongTRUE13524282011Shi, ZJ
Mutual Activation: Suzuki-Miyaura Coupling through Direct Cleavage of the sp(2) C-O Bond of Naphtholate
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Peking Univ6/24/2011FALSEFALSEFALSECsp2_ar-Csp2_arE-NuOBOHB(nep)ArylArylNaHIonic-HStrong-0.81_10.1002/anie.201412051,10.1002/chem.201103050,10.1002/anie.201510497,10.1021/ol503707m,10.1021/ja307045r,10.1021/acscatal.8b03436,10.1002/chem.201103784,10.1021/jacs.1c09797,10.1002/anie.201511486,10.1021/jacs.7b04973,10.1021/acscatal.6b00801,10.1016/j.tet.2012.04.005,10.1002/anie.201607646,10.1002/anie.201403823,10.1021/ol4011757,10.1021/ol502583h,10.1002/ejoc.201200444,10.1039/c4cc08426h,10.1021/ja5029793,10.1021/acs.orglett.6b02656,10.1021/ja210249h,10.1002/adsc.201400460,10.1021/ja413131m,10.1021/acs.orglett.6b0226510.1039/d1ra08771a,10.1021/jacs.1c12622,10.1021/jacs.1c09797,10.1002/chem.202101880,10.1002/anie.202106356,10.1021/jacs.1c03038,10.1021/acscatal.0c05557,10.1055/a-1349-3543,10.1021/acscatal.0c03334,10.1055/s-0040-1707269,10.1021/acs.chemrev.0c00088,10.1002/asia.202000763,10.1016/j.jcat.2020.06.034,10.1155/2020/1543081,10.1002/cjoc.201900506,10.1055/s-0039-1690740,10.1002/aoc.5383,10.1039/c9qo01095e,10.1002/anie.201908336,10.1021/acs.orglett.9b02504,10.1021/acs.orglett.9b02613,10.1016/j.jcat.2019.07.026,10.1007/3418_2018_19,10.1021/acs.accounts.8b00408,10.1021/acscatal.8b03436,10.1039/c8qo00729b,10.1021/acs.joc.8b02104,10.1021/acs.organomet.8b00199,10.1002/adsc.201800729,10.1021/jacs.8b04479,10.1016/j.jorganchem.2018.01.019,10.6023/cjoc201709041,10.1021/acs.organomet.8b00046,10.1002/aoc.4273,10.1002/ajoc.201700450,10.1002/cjoc.201700664,10.1021/acs.orglett.7b03753,10.2174/1385272822666180704143509,10.1055/s-0036-1588568,10.1055/s-0036-1589126,10.1055/s-0036-1590962,10.1021/jacs.7b04973,10.1021/jacs.7b03159,10.1021/jacs.7b03538,10.1002/anie.201611720,10.1021/jacs.6b10998,10.1021/acscatal.6b02964,10.1002/anie.201607646,10.1021/acs.joc.6b02093,10.1021/acs.orglett.6b02656,10.1002/chem.201604160,10.1021/acscatal.6b01687,10.1021/acscatal.6b01956,10.1021/acscatal.6b02124,10.1021/acs.orglett.6b02265,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1002/anie.201510497,10.1021/acs.joc.6b00289,10.1021/acs.joc.5b02849,10.1021/acscatal.5b02058,10.1002/anie.201511486,10.1016/bs.adomc.2016.07.001,10.1039/c5qo00395d,10.1002/anie.201506751,10.1021/jacs.5b08621,10.1021/jacs.5b08103,10.1002/anie.201505136,10.1002/adsc.201500515,10.1021/acs.orglett.5b01229,10.1016/j.tet.2015.02.088,10.1021/jacs.5b03955,10.1021/acs.accounts.5b00051,10.3390/molecules20057528,10.6023/A14120828,10.1016/j.jorganchem.2015.01.009,10.1002/anie.201412051,10.1021/ar500345f,10.1021/ja512498u,10.1021/ol503707m,10.1021/ol503560e,10.1039/C5QO00243E,10.1039/c5sc00305a,10.1039/c4cc08363f,10.1039/c4cc08426h,10.1039/c4cc10084k,10.1248/yakushi.14-00192,10.1021/ol502583h,10.1016/j.tetlet.2014.08.077,10.1002/adsc.201400460,10.1016/j.cclet.2014.04.019,10.1002/ejoc.201402475,10.1007/s11426-014-5138-3,10.1002/anie.201403894,10.1021/ol501744g,10.1002/anie.201403823,10.1021/ja5029793,10.1038/nature13274,10.1021/jo500675a,10.1515/pac-2014-5038,10.1021/ja412107b,10.1021/ja413131m,10.1021/ja4118413,10.1021/cs4009946,10.1021/ja410883p,10.6023/cjoc201307035,10.1021/ol403028a,10.1021/ja409803x,10.1002/asia.201300688,10.1021/ol4011757,10.1021/ja311940s,10.6023/A12110984,10.1007/3418_2012_42,10.1039/c3cs35521g,10.1002/ejoc.201200914,10.1021/ja3079362,10.1002/adsc.201200364,10.1021/ja307045r,10.1055/s-0032-1317076,10.1021/cs300028y,10.1002/ejoc.201200444,10.1002/ejoc.201200368,10.1016/j.tet.2012.04.005,10.1021/ol300671y,10.1002/chem.201103784,10.1021/ja210249h,10.1002/chem.201103050,10.1021/ja207759eKelly11/16/20212011FALSEFALSEFALSEFALSE50317097
30
227FALSEanie.20120252710.1002/anie.201202527https://sci-hub.wf/10.1002/anie.201202527https://doi.org/10.1002/anie.201202527NiC-O ActivationxGerryTRUE16621322012Jarvo, ER
Synthesis of Enantioenriched Triarylmethanes by Stereospecific Cross-Coupling Reactions
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Univ Calif Irvine6/27/2012Csp3-ring(s)-Csp2_arE-NuOMg
OCCOMe
MgXBenzylArylNo baseNo BaseStrong-0.24_10.1021/jacs.7b02326,10.1021/ol502583h,10.1021/ja311783k,10.1021/ja5029793,10.1002/anie.201511486,10.1021/ja5026485,10.1021/jacs.7b04973,10.1002/anie.201412051,10.1039/c8sc00609a,10.1002/anie.201308666,10.1039/c5sc03704b,10.1002/chem.201603436,10.1021/ol4011757,10.1021/jacs.6b08075,10.1002/ejic.201900692,10.1021/ja4034999,10.1002/anie.201503936,10.1021/acscatal.8b03436,10.1038/NCHEM.2741,10.1021/ja3089422,10.1021/ja507642610.6023/cjoc202106021,10.1016/j.jorganchem.2021.122068,10.1007/s11426-021-1077-4,10.1021/acs.inorgchem.1c01720,10.1039/c9cs00571d,10.1021/acs.organomet.1c00085,10.1055/s-0040-1720406,10.1021/acsomega.0c06358,10.1002/anie.202102192,10.1016/j.tetlet.2021.152947,10.1002/anie.202101682,10.1016/j.tetlet.2021.152862,10.1002/ajoc.202100016,10.1021/acs.orglett.0c04316,10.1021/acscatal.0c05484,10.1055/s-0040-1705987,10.1039/d0qo00825g,10.1021/acs.orglett.0c02765,10.1055/s-0040-1707115,10.1039/d0qo00402b,10.1021/acs.chemrev.9b00682,10.1002/aoc.5716,10.1007/s11426-019-9732-5,10.1021/acs.joc.9b03433,10.1039/d0nj00032a,10.1002/chem.202000215,10.1039/c9qo01391a,10.1002/anie.201912739,10.1021/acs.orglett.9b03475,10.1016/j.tetlet.2019.150955,10.1002/asia.201900960,10.1021/acs.orglett.9b02308,10.1002/ejic.201900692,10.1021/acs.orglett.9b01755,10.1002/ejoc.201900465,10.1016/j.tetlet.2019.05.003,10.1039/c9ob00628a,10.1021/acscatal.8b04357,10.1002/adsc.201801446,10.1021/acs.organomet.8b00720,10.1021/acscatal.8b03436,10.1039/c8cc07093h,10.1039/c8nj03955k,10.1002/anie.201806742,10.1021/acs.joc.8b01428,10.1055/s-0037-1609732,10.1016/j.jorganchem.2018.01.019,10.6023/cjoc201711045,10.1039/c8sc00609a,10.1002/cctc.201701601,10.1002/adsc.201800150,10.1002/chem.201800585,10.1021/acs.orglett.8b00169,10.1021/acs.orglett.8b00053,10.1002/chem.201705463,10.1016/j.tetlet.2017.11.049,10.1021/jacs.7b08326,10.1016/j.poly.2017.08.021,10.1002/ajoc.201700419,10.1055/s-0036-1588572,10.1021/acs.joc.7b02296,10.1039/c7ob02007d,10.1021/jacs.7b04973,10.1002/anie.201706868,10.1038/NCHEM.2741,10.1002/anie.201703380,10.1039/c7qo00097a,10.1039/c7ob00911a,10.1021/jacs.7b02326,10.1021/acs.joc.6b02769,10.1002/anie.201611720,10.1002/adsc.201600814,10.1055/s-0036-1588893,10.1002/chem.201605445,10.1016/j.poly.2016.10.033,10.1039/c6ra25429b,10.1016/j.tetlet.2016.10.087,10.1021/acscatal.6b02392,10.1002/chem.201603436,10.1002/cjoc.201600330,10.1021/acscatal.6b01681,10.1021/acscatal.6b01956,10.1021/acscatal.6b02124,10.1021/jacs.6b08075,10.1016/j.tet.2016.06.031,10.1021/jacs.6b06285,10.1002/slct.201600650,10.1002/adsc.201600590,10.1021/jacs.6b03384,10.1002/anie.201602075,10.1002/ejoc.201600385,10.1016/j.tet.2016.02.047,10.1002/anie.201600305,10.1002/anie.201511486,10.1016/bs.adomc.2016.07.001,10.1039/c6ob01638c,10.1039/c5sc03704b,10.1021/acs.joc.5b02557,10.1039/c5ob02167g,10.1021/acs.orglett.5b03455,10.1039/c6ra11116e,10.1002/anie.201505981,10.1002/chem.201503647,10.1021/acs.orglett.5b02410,10.1016/j.tet.2015.08.056,10.1021/jacs.5b08103,10.1002/anie.201505926,10.1021/acs.oprd.5b00148,10.1021/acs.chemrev.5b00162,10.1016/j.tet.2015.04.066,10.1002/anie.201503888,10.1002/anie.201503936,10.1021/acscatal.5b00909,10.1021/acs.accounts.5b00223,10.1021/acs.joc.5b00991,10.1021/acs.orglett.5b01030,10.1021/jacs.5b03277,10.1016/j.tetlet.2015.02.121,10.1021/jacs.5b03955,10.1016/j.tetlet.2015.03.054,10.1002/ajoc.201402275,10.1002/anie.201412051,10.1021/ja510980d,10.1021/ol503213z,10.1039/c4cc08559k,10.1016/S1872-2067(14)60217-5,10.1021/ja5109084,10.1016/j.poly.2014.03.028,10.1021/ol502583h,10.1021/ja5076426,10.1021/ol5024344,10.1016/j.tet.2014.03.039,10.1021/jo5010636,10.1021/ja5039616,10.1021/ja5026485,10.1002/anie.201403046,10.1021/ja5029793,10.1021/ja412159g,10.1021/jo4028598,10.6023/cjoc201310035,10.1002/anie.201308666,10.1021/ol403680c,10.1021/ja412107b,10.1021/ja410883p,10.1002/anie.201307019,10.1039/c4cs00206g,10.1002/chem.201303683,10.1016/j.tet.2013.05.001,10.1021/ol4011757,10.1021/ja4034999,10.1021/ol400690t,10.1021/ja311783k,10.1021/ja312087x,10.1021/ja3089422,10.1021/ol303130j,10.1002/anie.201301625,10.1002/chem.201203969,10.1021/ja3047816Kelly1/19/2022
31
160FALSEanie.20130839110.1002/anie.201308391https://sci-hub.wf/10.1002/anie.201308391https://doi.org/10.1002/anie.201308391NiC-O ActivationShihongTRUE8310662014Jamison, TF
Nickel-Catalyzed Mizoroki-Heck Reaction of Aryl Sulfonates and Chlorides with Electronically Unbiased Terminal Olefins: High Selectivity for Branched Products
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Achieving high selectivity in the Heck reaction of electronically unbiased alkenes has been a longstanding challenge. Using a nickel-catalyzed cationic Heck reaction, we were able to achieve excellent selectivity for branched products (19:1 in all cases) over a wide range of aryl electrophiles and aliphatic olefins. A bidentate ligand with a suitable bite angle and steric profile was key to obtaining high branched/linear selectivity, whereas the appropriate base suppressed alkene isomerization of the product. Although aryl triflates are traditionally used to access the cationic Heck pathway, we have shown that, by using triethylsilyl trifluoromethanesulfonate, we can effect a counterion exchange of the catalytic nickel complex, such that cheaper and more stable aryl chlorides, mesylates, tosylates, and sulfamates can be used to yield the same branched products with high selectivity.
MIT2/10/2014TRUEFALSETRUECsp2_ar-Csp2E-NuOHOTsHArylVinylDABCONitrogenNitrogen(neutral)Weak0.36_xxx10.1002/chem.201406457,10.1002/anie.201710241,10.1021/acscatal.9b02230,10.1039/d1cc00634g,10.1039/c5sc01589h,10.1021/acscatal.9b00744,10.1002/anie.202011036,10.1021/jacs.9b03280,10.1021/acscatal.5b00498,10.1039/c6ob01299j10.1021/acscatal.1c05441,10.1021/acscatal.1c04766,10.1038/s41929-021-00658-2,10.1021/jacs.1c03228,10.1039/d1ob00496d,10.1021/acscatal.1c00951,10.1039/d1cc00634g,10.1021/acs.orglett.1c00296,10.1002/anie.202011036,10.1002/adsc.202000820,10.1039/d0cc03966g,10.1021/acs.orglett.0c02909,10.1002/slct.202001578,10.1039/d0cc02142c,10.1021/acs.chemrev.9b00682,10.1002/ajoc.202000145,10.1016/j.tet.2020.131201,10.1021/acs.orglett.0c00983,10.1016/j.polymertesting.2020.106354,10.1021/acs.orglett.0c00061,10.1021/acscatal.9b03019,10.1021/acs.orglett.9b02577,10.1021/acs.orglett.9b02130,10.1021/acscatal.9b02230,10.3762/bjoc.15.176,10.1002/anie.201903890,10.1002/anie.201812534,10.1021/acs.orglett.9b00600,10.1021/jacs.9b03280,10.1021/acscatal.9b00744,10.1002/anie.201814572,10.1007/s11164-018-3671-y,10.1002/anie.201814493,10.1039/c8nj05503c,10.1021/jacs.8b10874,10.1016/j.tet.2018.10.025,10.1055/s-0037-1610161,10.1021/jacs.8b06966,10.1021/acs.orglett.8b01772,10.1021/jacs.8b03163,10.1002/ejoc.201800330,10.1021/acs.orglett.8b00583,10.1021/acs.orglett.8b00496,10.1016/j.cclet.2017.08.004,10.1021/acs.orglett.7b03713,10.1039/c7sc04351a,10.3390/catal8010023,10.1002/anie.201710241,10.1039/c7cc06881f,10.1002/anie.201707134,10.1002/anie.201706719,10.1021/acs.orglett.7b01858,10.1021/jacs.7b06340,10.1021/acs.orglett.7b01054,10.1021/jacs.7b00643,10.1002/adsc.201601105,10.14102/j.cnki.0254-5861.2011-1301,10.1021/acscatal.6b03277,10.1007/s10562-016-1880-9,10.1002/ejoc.201600955,10.1021/acs.organomet.6b00532,10.1002/anie.201606955,10.1039/c6cc07032a,10.1039/c6ob01299j,10.1039/c5cy02235e,10.1002/ejoc.201500734,10.1021/acscatal.5b01075,10.1021/jacs.5b05597,10.1021/acscatal.5b00498,10.1021/acs.accounts.5b00064,10.1055/s-0034-1379994,10.1002/chem.201406457,10.1021/acscatal.5b00072,10.1021/ol503748t,10.1039/c5dt01516b,10.1039/c5sc01589h,10.1039/c5cc05312a,10.1021/om500767p,10.1021/ol502953w,10.1038/nature13274,10.1039/c4cc06397jKelly11/5/2021FEB 102014FALSEFALSEFALSEFALSE5371858
32
202FALSEanie.20130866610.1002/anie.201308666https://sci-hub.wf/10.1002/anie.201308666https://doi.org/10.1002/anie.201308666NiC-O ActivationShihongTRUE11614322014Jarvo, ER
Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Grignard Reagents and Identification of Selective Anti-Breast-Cancer Agents
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Alkyl Grignard reagents that contain beta-hydrogen atoms were used in a stereospecific nickel-catalyzed cross-coupling reaction to form C(sp(3))-C(sp(3)) bonds. Aryl Grignard reagents were also utilized to synthesize 1,1-diarylalkanes. Several compounds synthesized by this method exhibited selective inhibition of proliferation of MCF-7 breast cancer cells.
Univ Calif Irvine2/24/2014TRUETRUEFALSECsp3-ring(s)-Csp3E-NuOMgOMeMgXBenzylAlkylNo baseNo BaseStrong-0.28_x10.1021/jacs.7b04973,10.1021/ol502583h,10.1002/anie.201402922,10.1039/c7cc06106d,10.1039/c8sc00609a,10.1021/jacs.8b02134,10.1021/ol502682q,10.1002/anie.201805611,10.1021/ja5076426,10.1021/ja5026485,10.1021/acs.orglett.6b02656,10.1021/ol503707m,10.1038/s41467-019-11392-6,10.1021/jacs.6b0325310.1002/ejoc.202101535,10.1021/acs.inorgchem.1c03108,10.6023/cjoc202106021,10.3390/molecules26195947,10.1002/anie.202110459,10.1016/j.jorganchem.2021.122068,10.1021/acs.orglett.1c02532,10.1021/acs.accounts.1c00329,10.1039/c9cs00571d,10.6023/cjoc202101049,10.1021/acs.orglett.1c01457,10.1016/j.tetlet.2021.152947,10.1002/anie.202101682,10.1021/acs.orglett.0c04316,10.1246/bcsj.20200321,10.1039/d0cc05003b,10.1055/s-0040-1705987,10.1021/jacs.0c09008,10.1038/s41467-020-19194-x,10.1002/anie.202008262,10.1002/anie.202010386,10.1007/s11426-019-9732-5,10.1016/j.chempr.2020.01.009,10.1021/acs.joc.0c00008,10.1055/s-0039-1690718,10.1021/acs.orglett.9b04392,10.1002/jccs.201900450,10.1002/adsc.201901398,10.1016/j.trechm.2019.08.004,10.1021/acs.orglett.9b03475,10.1021/acscatal.9b02636,10.1002/ijch.201900071,10.1021/jacs.9b06608,10.1002/anie.201907045,10.1038/s41467-019-11392-6,10.1021/acs.oprd.9b00199,10.1007/s00706-019-2364-6,10.1002/anie.201900228,10.1002/anie.201811343,10.1039/c8ob02864h,10.1021/acs.organomet.8b00720,10.24820/ark.5550190.p010.866,10.1002/adsc.201801135,10.1039/c8cc07093h,10.1021/acs.joc.8b01763,10.1002/anie.201806742,10.1021/jacs.8b05374,10.1002/anie.201805611,10.1039/c8cc03541e,10.1021/acs.orglett.8b01323,10.1021/acs.joc.8b00728,10.1016/j.jorganchem.2018.01.019,10.1002/chem.201801241,10.1039/c8sc00609a,10.1002/cctc.201701601,10.1002/chem.201800744,10.1021/acs.orglett.8b00169,10.1021/jacs.8b02134,10.1021/jacs.7b13220,10.1002/chem.201705463,10.1021/acs.accounts.7b00432,10.24820/ark.5550190.p010.746,10.1021/acscatal.7b03465,10.1055/s-0036-1590962,10.1002/asia.201701224,10.1021/acs.organomet.7b00632,10.1021/jacs.7b04973,10.1002/anie.201706631,10.1039/c7cc06106d,10.1002/anie.201706868,10.1021/acs.orglett.7b02287,10.1021/acs.orglett.7b01510,10.1002/anie.201703380,10.1021/acs.orglett.7b01022,10.1021/jacs.7b01705,10.1038/s41570-017-0025,10.1002/chem.201605445,10.1002/chem.201603481,10.1021/acs.orglett.6b02656,10.1002/adsc.201600590,10.1021/jacs.6b04566,10.1002/anie.201602075,10.1021/jacs.6b03253,10.1002/anie.201600697,10.1021/acs.orglett.6b00453,10.1021/acssuschemeng.5b01282,10.1016/bs.adomc.2016.07.001,10.1016/bs.aihch.2016.04.002,10.1039/c6gc00163g,10.1002/chem.201503647,10.1021/acs.orglett.5b02410,10.1021/acs.oprd.5b00148,10.1021/acs.chemrev.5b00162,10.1016/j.tet.2015.04.066,10.1515/znb-2015-0053,10.1021/acs.accounts.5b00223,10.1016/j.tetlet.2015.05.006,10.1002/adsc.201400850,10.1021/jacs.5b03955,10.1021/ol503707m,10.1021/ja510980d,10.1039/c4cc10084k,10.1002/anie.201402922,10.1021/ol502583h,10.1021/ol502682q,10.1021/ja5076426,10.1021/jo5010636,10.1021/ja5026485,10.1021/ol500902p,10.1039/c4cs00206gKelly11/5/2021FEB 242014FALSEFALSEFALSEFALSE5392422
33
36FALSEanie.20201204810.1002/anie.202012048https://sci-hub.wf/10.1002/anie.202012048https://doi.org/10.1002/anie.202012048NiC-N ActivationLongTRUE101542021Garg, NK
Reductive Arylation of Amides via a Nickel-Catalyzed Suzuki-Miyaura-Coupling and Transfer-Hydrogenation Cascade
ANGEW CHEM INT EDIT
We report a means to achieve the addition of two disparate nucleophiles to the amide Carbonyl carbon in a single operational step. Our method takes advantage of non-precious-metal catalysis and allows for the facile conversion of amides to chiral alcohols via a one-pot Suzuki-Miyaura cross-coupling/transfer-hydrogenation process. This study is anticipated to promote the development of new transformations that allow for the conversion of carboxylic acid derivatives to functional groups bearing stereogenic centers via cascade processes.
Univ Calif Los Angeles
2/1/2021Csp2-Csp2_arE-NuNB
N(Bn)Boc
Bpin
Carbonyl
ArylIonic-PO4_10.1039/d1ob02414k,10.1039/d1ob02349g,10.1039/d1qo01240a,10.1016/S1872-2067(21)63853-6,10.1021/acs.oprd.1c00241,10.1002/chem.202101880,10.1002/ejoc.202100660,10.6023/cjoc202100028Long2/17/2022
34
184FALSEanie.20140292210.1002/anie.201402922https://sci-hub.wf/10.1002/anie.201402922https://doi.org/10.1002/anie.201402922NiC-O ActivationShihongTRUE10023892014Rueping, M
Metal-Catalyzed Dealkoxylative C-aryl-C-sp3 Cross-Coupling-Replacement of Aromatic Methoxy Groups of Aryl Ethers by Employing a Functionalized Nucleophile
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
The direct replacement of aromatic methoxy groups with activated carbon nucleophiles would give rise to novel synthetic pathways for targeted and diversity-oriented syntheses. We demonstrate here that this transformation can be achieved in a one-step reaction involving a bifunctional organolithium nucleophile in combination with a C-Ar-OMe bond-cleaving nickel catalyst. The resulting products are stable, alpha-CH active, and suitable for various further modifications.
Rhein Westfal TH Aachen
11/17/2014Ni(0) caseCsp2_ar-Csp3E-NuOLiOMeLiAryl
Csp3-Si
No baseNo BaseStrong-0.28_10.1021/acscatal.6b00801,10.1002/anie.201806790,10.1021/acscatal.7b00941,10.1002/chem.201603436,10.1021/acs.orglett.7b00556,10.1039/c9sc00783k,10.1039/c8sc00609a,10.1039/c4cc08187k,10.1021/acs.orglett.8b01021,10.1021/jacs.7b02326,10.1021/acs.orglett.6b02656,10.1021/jacs.7b04973,10.1002/anie.201510497,10.1002/chem.201702867,10.1021/acscatal.7b01058,10.1021/acs.orglett.5b02200,10.1002/chem.201505106,10.1021/ol503707m,10.1021/jacs.1c09797,10.1021/jacs.6b03253,10.1021/acscatal.8b03436,10.1002/anie.201607646,10.1246/cl.15093610.1039/d1ra08771a,10.1021/jacs.1c09797,10.1002/anie.202110785,10.1039/d1qo00811k,10.1039/d1qo00549a,10.1002/chem.202101090,10.1021/jacs.1c03038,10.1055/a-1467-2494,10.6023/cjoc202006075,10.1021/acs.orglett.0c03507,10.1021/acs.chemrev.0c00088,10.1002/asia.202000763,10.1039/d0sc01585g,10.1002/cjoc.201900506,10.1039/c9qo01428d,10.1002/chem.201904842,10.6023/A19050193,10.1002/adsc.201900686,10.1039/c9nj01748h,10.1002/adsc.201801713,10.1002/anie.201902315,10.1039/c9sc00783k,10.1038/s41929-019-0250-6,10.1246/bcsj.20180333,10.1007/3418_2018_19,10.1021/acscatal.8b03436,10.1021/acs.joc.8b02104,10.1039/c8cc06768f,10.1021/acs.orglett.8b02351,10.1039/c8cc03665a,10.1002/anie.201806790,10.1002/chem.201704670,10.1016/j.jorganchem.2018.01.019,10.1039/c8sc00609a,10.1021/acs.orglett.8b01021,10.1021/acs.accounts.8b00023,10.1021/acscatal.8b01224,10.1038/s41467-018-03928-z,10.1002/cjoc.201700664,10.1039/c7cc08709h,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.1002/chem.201703266,10.1055/s-0036-1591495,10.1021/acs.orglett.7b03152,10.1039/c7sc02578e,10.1021/jacs.7b04973,10.1002/chem.201702867,10.1021/acscatal.7b02025,10.1248/cpb.c17-00487,10.1021/acs.orglett.7b01905,10.1021/acscatal.7b00941,10.1021/acscatal.7b01058,10.1021/jacs.7b02326,10.1002/ejoc.201700514,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1002/anie.201612624,10.1021/jacs.6b10998,10.1021/acscatal.6b02964,10.1002/anie.201607646,10.1021/acs.orglett.6b02656,10.1002/ajoc.201600411,10.1021/acs.orglett.6b02784,10.1021/acscatal.6b01687,10.1002/chem.201604452,10.1002/chem.201604504,10.1002/chem.201603436,10.1021/acs.organomet.6b00638,10.1002/anie.201604696,10.1007/s41061-016-0043-1,10.1021/acscatal.6b00801,10.1021/jacs.6b03253,10.1002/anie.201510497,10.1002/chem.201505106,10.1016/bs.adomc.2016.07.001,10.1039/c6cc01312k,10.1021/acscatal.5b02089,10.1246/cl.150936,10.1002/anie.201506751,10.1021/jacs.5b08621,10.1021/jacs.5b10119,10.1002/chem.201502114,10.1021/acs.joc.5b01540,10.1021/acs.orglett.5b02200,10.1021/acs.orglett.5b01229,10.1016/j.tetlet.2015.05.025,10.1021/acs.accounts.5b00051,10.1002/chem.201500627,10.1021/acs.orglett.5b00905,10.1021/ol503707m,10.1039/c5qo00001g,10.1039/c4cc09337b,10.1039/c4cc08187kKelly12/1/2021
35
219FALSEanie.20140382310.1002/anie.201403823https://sci-hub.wf/10.1002/anie.201403823https://doi.org/10.1002/anie.201403823NiC-O ActivationKellyTRUE14419492014Yamaguchi, J
Nickel-Catalyzed alpha-Arylation of Ketones with Phenol Derivatives
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
The nickel-catalyzed alpha-arylation of ketones with readily available phenol derivatives (esters and carbamates) provides access to useful alpha-arylketones. For this transformation, 3,4-bis(dicyclohexylphosphino)thiophene (dcypt) was identified as a new, enabling, air-stable ligand for this transformation. The intermediate of an assumed C-O oxidative addition was isolated and characterized by X-ray crystal-structure analysis.
Nagoya Univ6/1/2014TRUEFALSEFALSECsp2_ar-Csp3E-NuOHOPivHArylAlkylK3PO4Ionic-PO4Medium0.33_x10.1021/acs.orglett.7b00556,10.1021/acs.orglett.6b02265,10.1021/acscatal.0c00291,10.1021/acscatal.6b00801,10.1002/chem.201406457,10.1021/jacs.5b02945,10.1021/acscatal.7b00941,10.1021/ol501707z,10.1039/c6ob01299j,10.1039/c5sc02942b,10.1021/jacs.7b04973,10.1021/acs.orglett.8b02256,10.1002/anie.202006826,10.1002/anie.201412051,10.1021/acs.orglett.6b00819,10.1021/acs.orglett.6b02656,10.1021/acscatal.8b03436,10.1002/anie.202004116,10.1039/c4cc08426h10.1039/d1ra08771a,10.1021/acs.joc.1c02446,10.1021/acs.joc.1c02446,10.1002/cctc.202101237,10.1002/aoc.6493,10.1055/a-1677-4881,10.1021/jacs.1c04215,10.1016/j.tetlet.2021.153208,10.1021/acs.orglett.1c01189,10.1016/j.ccr.2021.213889,10.1055/a-1416-4924,10.1055/a-1349-3543,10.2174/1385272825666210531110403,10.1016/j.tetlet.2020.152629,10.1016/j.tetlet.2020.152532,10.1002/cjoc.202000319,10.1055/s-0040-1705943,10.1021/acs.chemrev.0c00088,10.1002/asia.202000763,10.1002/cctc.202000876,10.1002/anie.202006826,10.1039/d0dt02063j,10.1002/adsc.202000622,10.1021/acs.chemrev.9b00682,10.1126/sciadv.aba7614,10.1002/anie.202004116,10.1039/d0sc01585g,10.1021/acs.organomet.0c00338,10.1002/cjoc.201900506,10.1002/ejoc.202000142,10.1002/ejoc.201901883,10.1021/acscatal.0c00291,10.1021/acscatal.9b04212,10.1021/acs.orglett.9b02830,10.1021/acs.organomet.9b00340,10.1039/c9ra02394a,10.1002/cctc.201900254,10.6023/cjoc201809027,10.1021/acs.organomet.8b00451,10.1007/3418_2018_19,10.1021/acscatal.8b03436,10.1021/acs.orglett.8b02972,10.1002/anie.201804955,10.1021/acs.orglett.8b02256,10.1002/asia.201800478,10.1002/adsc.201800729,10.1055/s-0037-1609963,10.1021/jacs.8b04479,10.1039/c8ob01034j,10.1002/ajoc.201800207,10.1016/j.tetlet.2018.04.076,10.1246/cl.180226,10.1016/j.jorganchem.2018.01.019,10.1021/acs.orglett.8b01233,10.1021/acs.orglett.8b00974,10.1002/adsc.201701596,10.1021/acs.orglett.8b00674,10.1002/aoc.4284,10.1039/c7cc08181b,10.1021/acs.orglett.7b03713,10.1021/acs.orglett.8b00080,10.1039/c7cc08709h,10.1039/c7nj03989a,10.1021/acs.orglett.7b03669,10.1039/c8ra04984j,10.1055/s-0036-1589120,10.1039/c7cs00182g,10.1021/jacs.7b04973,10.1039/c7sc02692g,10.1021/acscatal.7b00941,10.1021/acs.orglett.7b00885,10.1016/j.tet.2017.02.021,10.1021/acs.joc.6b02701,10.1021/acs.orglett.7b00556,10.1246/bcsj.20160365,10.1002/adsc.201601105,10.1002/anie.201611720,10.1021/jacs.7b00049,10.1021/acs.joc.6b02693,10.1002/chem.201700680,10.1246/cl.161001,10.1039/c6cc08392g,10.1021/acscatal.6b02964,10.1021/acs.orglett.6b02656,10.1021/acscatal.6b01687,10.1021/acs.orglett.6b02556,10.1016/j.jorganchem.2016.07.026,10.1021/acs.orglett.6b02516,10.1021/acs.orglett.6b02265,10.1021/acs.orglett.6b02094,10.1002/chem.201602150,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1016/j.jorganchem.2016.03.027,10.1021/acs.orglett.6b00819,10.1021/acs.joc.6b00289,10.1246/cl.160133,10.1021/acs.joc.6b00203,10.1002/anie.201511487,10.1002/anie.201600248,10.1016/j.tetlet.2016.02.069,10.1002/chem.201504844,10.1002/adsc.201500822,10.1016/bs.adomc.2016.07.001,10.1039/c6ob01299j,10.1039/c5cc10005d,10.1039/c6ra07130a,10.1002/chem.201503414,10.1002/anie.201506751,10.1021/acs.organomet.5b00733,10.1002/anie.201503204,10.1021/acs.orglett.5b01229,10.1055/s-0034-1380813,10.1021/jacs.5b04548,10.1021/jacs.5b02945,10.1002/chem.201500560,10.1016/j.tetlet.2015.02.061,10.1038/ncomms8508,10.1021/acs.accounts.5b00051,10.1021/acscatal.5b00306,10.1016/j.inoche.2015.02.018,10.1002/anie.201412051,10.1002/chem.201406457,10.1021/acscatal.5b00072,10.1021/ol503607h,10.1021/ja512498u,10.1039/c5sc02942b,10.1039/c5cy00876j,10.1039/c5ob00149h,10.1007/s10562-014-1449-4,10.1039/c4cc08426h,10.1039/c5cy00851d,10.1039/c4cc10084k,10.1039/c4dt01808g,10.1021/ol501707z,10.1039/c4cs00206gKelly11/9/2021JUN2014FALSEFALSEFALSEFALSE53266791
36
154FALSEanie.20141087510.1002/anie.201410875https://sci-hub.wf/10.1002/anie.201410875https://doi.org/10.1002/anie.201410875NiC-O ActivationGerryTRUE8410382015
Stradiotto, M
Nickel-Catalyzed Monoarylation of Ammonia
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Structurally diverse (hetero)aryl chloride, bromide, and tosylate electrophiles were employed in the Ni-catalyzed monoarylation of ammonia, including chemoselective transformations. The employed JosiPhos/[Ni(cod)(2)]catalyst system enables the use of commercially available stock solutions of ammonia, or the use of ammonia gas in these reactions, thereby demonstrating the versatility and potential scalability of the reported protocol. Proof-of-principle experiments established that air-stable [(JosiPhos)NiCl2] precatalysts can be employed successfully in such transformations.
Dalhousie Univ3/16/2015Csp2_ar-Nsp3E-NuOHOTsHHetNH2NaOtBuIonic-OtBuWeak0.36_x10.1021/acscatal.0c00393,10.1002/anie.202200352,10.1002/chem.201605095,10.1039/c5sc01589h,10.1021/acscatal.8b01879,10.1038/ncomms11073,10.1021/acs.orglett.7b00556,10.1039/c5sc03704b,10.1002/anie.202006826,10.1021/jacs.0c0028610.1002/anie.202200352,10.1021/acscatal.1c05386,10.1021/acscatal.1c05386,10.2533/chimia.2021.943,10.1021/acs.inorgchem.1c01720,10.1021/acs.organomet.1c00369,10.1016/j.tetlet.2021.153099,10.1055/s-0039-1691241,10.1021/acs.orglett.0c02672,10.1002/anie.202006826,10.1021/acs.chemrev.9b00682,10.1021/acs.orglett.0c01600,10.1021/acscatal.0c00393,10.1021/jacs.0c00286,10.1007/s13204-019-01133-y,10.1002/chem.201903696,10.1021/acscatal.9b03715,10.1021/acs.oprd.9b00226,10.1021/acs.orglett.9b01968,10.1002/chem.201902147,10.1002/anie.201900095,10.1002/adsc.201801661,10.1021/acs.inorgchem.8b03489,10.1039/c8ob02708k,10.1021/jacs.8b12495,10.1021/acs.organomet.8b00451,10.1021/acs.organomet.8b00605,10.1021/acs.jced.8b00719,10.1021/acs.organomet.8b00567,10.1002/ejoc.201800341,10.1021/acscatal.8b01879,10.1039/c8sc01256c,10.1021/acs.joc.8b00592,10.1021/acscatal.8b01005,10.1021/acscatal.8b00856,10.1021/acs.orglett.8b00646,10.1021/acs.orglett.7b03560,10.1021/acscatal.7b03215,10.1002/ajoc.201700464,10.1021/acs.oprd.7b00285,10.6023/cjoc201705044,10.1039/c7ob01791j,10.1002/adsc.201700672,10.1055/s-0036-1588806,10.1055/s-0036-1590819,10.1002/ejoc.201700660,10.1039/c7ob00841d,10.1039/c7dt01805c,10.1002/ejic.201700057,10.1021/acs.orglett.7b00556,10.1016/j.tetlet.2017.02.073,10.1002/adsc.201601105,10.1021/acscatal.6b02988,10.1021/acs.organomet.6b00885,10.1055/s-0036-1588371,10.1021/acs.organomet.6b00830,10.1002/chem.201605476,10.1002/chem.201605095,10.1021/acscatal.6b02576,10.1002/anie.201606979,10.1021/acs.organomet.6b00650,10.1002/tcr.201500305,10.1021/jacs.6b03855,10.6023/cjoc201601007,10.1021/acs.joc.6b00883,10.1038/ncomms11073,10.1039/c5dt03961d,10.1021/acs.joc.5b02448,10.1039/c5sc03704b,10.1016/j.tetlet.2015.10.096,10.1021/acs.orglett.5b03230,10.1021/acs.oprd.5b00314,10.1002/adsc.201500461,10.1002/ejoc.201500734,10.1002/chem.201501453,10.1021/acscatal.5b00606,10.1002/anie.201500404,10.1071/CH15459,10.1039/c5sc01589hKelly1/5/2022
37
151FALSEanie.20141205110.1002/anie.201412051https://sci-hub.wf/10.1002/anie.201412051https://doi.org/10.1002/anie.201412051NiC-O ActivationKellyTRUE7913182015Martin, R
Nickel-Catalyzed Enantioselective C-C Bond Formation through C-sp2-O Cleavage in Aryl Esters
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
We report the first enantioselective C-C bond formation through C-O bond cleavage using aryl ester counterparts. This method is characterized by its wide substrate scope and results in the formation of quaternary stereogenic centers with high yields and asymmetric induction.
Inst Chem Res Catalonia ICIQ
3/23/2015TRUEFALSEFALSECsp2_ar-Csp3E-NuOHOPivHArylAlkylNaOtBuIonic-OtBuMedium0.33_10.1021/jacs.7b04973,10.1021/acs.orglett.6b02265,10.1039/c6ob01299j,10.1021/jacs.5b02945,10.1021/acs.orglett.6b00819,10.1021/acscatal.6b00365,10.1039/c5sc01589h,10.1021/acscatal.7b00941,10.1002/anie.202006826,10.1002/anie.202004116,10.1021/acs.orglett.7b00556,10.1021/acscatal.8b03436,10.1021/acscatal.7b0105810.1021/acs.orglett.1c02093,10.1002/anie.202106109,10.1002/anie.202103465,10.1021/acs.organomet.1c00085,10.1002/anie.202101668,10.1002/cjoc.202000319,10.1021/acs.orglett.0c02913,10.1021/acs.chemrev.0c00088,10.1002/asia.202000763,10.1021/acs.joc.0c01768,10.1002/anie.202006826,10.1021/acs.chemrev.9b00682,10.1002/anie.202004116,10.1021/acs.orglett.0c01129,10.1039/d0sc01585g,10.1002/cjoc.201900506,10.1021/acscatal.9b04480,10.1021/jacs.9b08586,10.1021/acs.orglett.9b03170,10.1021/acs.orglett.9b02830,10.1039/c9ra02394a,10.1021/acscatal.8b04357,10.6023/cjoc201809027,10.1021/acs.organomet.8b00720,10.1007/3418_2018_19,10.1021/acscatal.8b03436,10.1002/anie.201807302,10.1039/c8qo00510a,10.1055/s-0037-1609963,10.1039/c8dt01857j,10.1039/c8sc00742j,10.1038/s41467-018-04480-6,10.1016/j.jorganchem.2018.01.019,10.1021/acs.orglett.7b03713,10.1039/c7cc08709h,10.1021/acs.orglett.7b03669,10.1021/acs.joc.7b02588,10.1039/c8ra04984j,10.1055/s-0036-1590923,10.1055/s-0036-1588568,10.1055/s-0036-1589120,10.1055/s-0036-1590962,10.1021/jacs.7b10365,10.1021/jacs.7b04973,10.1021/acscatal.7b00941,10.1021/acscatal.7b01058,10.1021/acs.orglett.7b01070,10.1002/anie.201612385,10.1021/acs.orglett.7b00556,10.1002/adsc.201601105,10.1002/anie.201611720,10.1002/chem.201700680,10.1021/acscatal.6b02988,10.1021/jacs.6b10998,10.1021/acscatal.6b03040,10.1021/acscatal.6b02964,10.1002/chem.201604061,10.1002/anie.201606955,10.1021/acs.orglett.6b02265,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acs.orglett.6b00819,10.1021/jacs.6b01214,10.1021/acscatal.6b00365,10.1002/chem.201504959,10.1002/adsc.201500822,10.1016/bs.adomc.2016.07.001,10.1039/c6ob01299j,10.1039/c5cc10005d,10.1039/c6ra07130a,10.1002/anie.201504524,10.1002/anie.201503204,10.1055/s-0034-1380813,10.1021/jacs.5b02945,10.1039/c5sc01589hKelly11/4/2021MAR 232015FALSEFALSEFALSEFALSE54134075
38
176FALSEanie.20150393610.1002/anie.201503936https://sci-hub.wf/10.1002/anie.201503936https://doi.org/10.1002/anie.201503936NiC-O ActivationLong17-FebTRUE999452015Doyle, AG
Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
A new substrate class for nickel-catalyzed C(sp(3)) cross-coupling reactions is reported. alpha-Oxy radicals generated from benzylic acetals, TMSCl, and a mild reductant can participate in chemoselective cross-coupling with aryl iodides using a 2,6-bis(N-pyrazolyl)pyridine (bpp)/Ni catalyst. The mild, base-free conditions are tolerant of a variety of functional groups on both partners, thus representing an attractive C-C bond-forming approach to dialkyl ether synthesis. Characterization of a [(bpp)NiCl] complex relevant to the proposed catalytic cycle is also described.
Princeton Univ8/17/2015TRUETRUETRUEyCsp3-ring(s)-Csp2_arE-EOXOMeI
Csp3-(Aryl)(OR)
ArylNo baseNo BaseStrong-0.28_xxx10.1002/anie.202110391,10.1039/c9sc03347e,10.1039/c8sc00609a,10.1021/jacs.7b03448,10.1021/acs.orglett.6b00658,10.1021/jacs.0c13093,10.1021/jacs.9b05224,10.1039/c7sc03140h,10.1038/NCHEM.274110.1039/d2cc00717g,10.1021/acscatal.1c05801,10.1021/jacs.1c12199,10.1055/s-0041-1737762,10.1007/s11426-021-1172-x,10.1021/jacs.1c10932,10.1002/anie.202110391,10.1002/hlca.202100177,10.6023/cjoc202106021,10.1021/acscatal.1c04143,10.1021/acs.orglett.1c02893,10.1021/acs.orglett.1c03066,10.1021/acs.orglett.1c03210,10.1039/d1sc03712a,10.1002/cssc.202101184,10.1021/jacs.1c03763,10.3390/catal11070858,10.1039/c9cs00571d,10.1021/acs.joc.1c00806,10.1021/jacs.1c03827,10.1021/acscatal.1c01416,10.1246/bcsj.20200364,10.1021/jacs.1c01086,10.1021/jacs.0c13093,10.1021/acs.accounts.0c00694,10.1039/d0cc07216h,10.1021/jacs.0c09922,10.1055/s-0040-1707342,10.1055/s-0040-1705972,10.1039/d0cc05306f,10.1021/acscatal.0c03237,10.1039/d0dt02964e,10.1021/acscatal.0c02584,10.1002/ejic.202000782,10.1021/acscatal.0c01842,10.1021/jacs.0c05254,10.1002/anie.202003359,10.1002/ejic.202000150,10.1016/j.chempr.2019.12.026,10.1002/adsc.201901139,10.1039/c9ob02691f,10.1021/acs.orglett.9b03899,10.1002/chem.201904545,10.1039/c9ob02129a,10.1039/c9sc03347e,10.1021/acs.joc.9b01556,10.1021/acs.orglett.9b02273,10.1021/jacs.9b02973,10.1021/jacs.9b05224,10.1246/cl.190405,10.1039/c9ob00628a,10.1021/acs.orglett.9b00692,10.1021/jacs.8b13709,10.1021/jacs.8b13652,10.1039/c8sc04335c,10.1002/chem.201805682,10.1021/acs.inorgchem.8b02960,10.1021/acscatal.8b04348,10.1039/c8qo01044g,10.1021/acscatal.8b03930,10.1021/acscatal.8b02784,10.1002/anie.201803228,10.1002/anie.201802563,10.1039/c8sc00609a,10.1021/acsomega.8b00159,10.1016/j.ica.2017.12.032,10.1021/acs.orglett.8b00408,10.1039/c8cc00001h,10.1021/jacs.7b12212,10.1039/c7sc03140h,10.1021/acs.organomet.7b00657,10.3762/bjoc.13.263,10.1055/s-0036-1590838,10.1021/jacs.7b06469,10.1039/c7cs00216e,10.1021/acs.orglett.7b02076,10.1038/NCHEM.2741,10.1002/anie.201701552,10.1021/jacs.7b03195,10.1021/jacs.7b03448,10.1016/j.poly.2016.10.005,10.1038/s41570-017-0025,10.1021/acs.organomet.6b00769,10.1021/acs.joc.6b02830,10.1002/anie.201607959,10.1002/anie.201606513,10.1055/s-0035-1560439,10.1055/s-0035-1562442,10.1021/acs.joc.6b01034,10.1007/s41061-016-0042-2,10.1021/acs.orglett.6b01134,10.1021/acs.orglett.6b00658Kelly11/9/2021AUG 172015FALSEFALSEFALSEFALSE54349876
39
86FALSEanie.20150749410.1002/anie.201507494https://sci-hub.wf/10.1002/anie.201507494https://doi.org/10.1002/anie.201507494NiC-O ActivationShihongTRUE523472016Walsh, PJ
Nickel-Catalyzed Allylic Alkylation with Diarylmethane Pronucleophiles: Reaction Development and Mechanistic Insights
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Palladium-catalyzed allylic substitution reactions are among the most efficient methods to construct C-C bonds between sp(3)-hybridized carbon atoms. In contrast, much less work has been done with nickel catalysts, perhaps because of the different mechanisms of the allylic substitution reactions. Palladium catalysts generally undergo substitution by a soft-nucleophile pathway, wherein the nucleophile attacks the allyl group externally. Nickel catalysts are usually paired with hard nucleophiles, which attack the metal before C-C bond formation. Introduced herein is a rare nickel-based catalyst which promotes substitution with diarylmethane pronucleophiles by the soft-nucleophile pathway. Preliminary studies on the asymmetric allylic alkylation are promising.
Univ Penn1/18/2016TRUEFALSEFALSECsp3-Csp3-ring(s)E-NuOHOBocHAllylBenzylKN(SiMe3)2IonicNitrogen(neutral)Medium0.31_x10.1002/chem.201603436,10.1002/anie.201703486,10.1039/c7sc05216b10.1021/jacs.1c11712,10.1002/ejic.202100820,10.3762/bjoc.17.167,10.1021/acscatal.1c03449,10.1055/s-0040-1720446,10.3390/catal11050526,10.1039/d1sc00972a,10.1016/j.tetlet.2021.152916,10.1039/d0sc03304a,10.1039/d0cc04512h,10.1002/asia.202000730,10.1021/acs.chemrev.9b00682,10.1039/c9gc04306c,10.1021/acs.orglett.0c01109,10.1021/jacs.9b12706,10.1039/c9ob01559k,10.1021/acs.orglett.9b04355,10.1002/anie.201912882,10.1021/acs.orglett.9b03633,10.1021/jacs.9b08734,10.1002/asia.201900960,10.1021/acs.orglett.9b02728,10.1021/acs.joc.9b01293,10.1002/anie.201904156,10.1021/acs.orglett.8b04030,10.1002/ejoc.201801596,10.1002/adsc.201801035,10.6023/cjoc201809037,10.1038/s41467-018-05638-y,10.1002/anie.201802821,10.1021/jacs.7b12806,10.1002/anie.201713165,10.1039/c8ob00687c,10.1002/ajoc.201800057,10.1039/c7sc05216b,10.1021/acs.joc.7b02375,10.1002/asia.201701224,10.1002/anie.201703486,10.6023/cjoc201702036,10.1002/anie.201700433,10.1016/j.tetlet.2016.12.056,10.1080/00397911.2017.1339803,10.1016/j.tetlet.2016.11.044,10.1021/jacs.6b11205,10.1002/chem.201603436,10.1039/c6ra19069c,10.1039/c6ra15665g11/5/2021JAN 182016FALSEFALSEFALSEFALSE5531070
40
43FALSEacscatal.0c0024610.1021/acscatal.0c00246https://sci-hub.wf/10.1021/acscatal.0c00246https://doi.org/10.1021/acscatal.0c00246NiC-N ActivationLongTRUE15122020Li, C
Nickel-Catalyzed Direct Acylation of Aryl and Alkyl Bromides with AcylimidazolesACS CATAL
A modular method for the acylation of aryl and alkyl halides is reported herein. The transformation relies on acylimidazoles, easy-to-prepare and flexible species derived from abundant carboxylic acids, as viable cross-coupling partners for the Ni-catalyzed acylation. Careful examination revealed a remarkable mechanism: the amide C-N bond of primary and secondary imidazolides can be activated by single-electron reduction, representing a major departure from other reported amide C-N bond activation reactions. Extensive mechanistic studies also revealed an intriguing CO-extrusion-recombination phenomenon. This cross-coupling reaction between two electrophiles features a broad substrate scope bearing a wide gamut of functionalities. The practicality of this atypical transformation was demonstrated in the syntheses of 3-furyl natural products, which are difficult to access using traditional organometallic chemistry.
Peking Union Med Coll & Chinese Acad Med Sci
3/20/2020TRUETRUEFALSEYCsp2-Csp2_arE-ENXImBr
Carbonyl
ArylNo baseNo BaseE-HUnique_xxx10.1002/anie.20211039110.1002/adsc.202200003,10.1002/anie.202114731,10.1002/anie.202110391,10.1002/chem.202103486,10.1021/jacs.1c07851,10.1021/acs.chemrev.1c00225,10.1002/asia.202100691,10.1002/anie.202014660,10.1021/acs.orglett.0c03342,10.1055/s-0040-1707301,10.1016/j.trechm.2020.08.001,10.1021/acs.orglett.0c01488Long10/31/2021MAR 202020FALSEFALSEFALSEFALSE1063895
41
44FALSEacscatal.0c0135610.1021/acscatal.0c01356https://sci-hub.wf/10.1021/acscatal.0c01356https://doi.org/10.1021/acscatal.0c01356NiC-N ActivationGerryTRUE161#N/A2020Zhang, WB
Asymmetric Allylic Alkylation of beta-Ketoesters via C-N Bond Cleavage of N-Allyl-N-methylaniline Derivatives Catalyzed by a Nickel-Diphosphine SystemACS CATAL
Nickel complexes bearing chiral diphosphine ligands, such as (S)-Tol-MeO-BIPHEP and (S)-H-8-BINAP, serve as efficient catalysts for asymmetric allylic alkylation (AAA) of beta-ketoesters, using allylic amines as ally! sources. The reactions proceed with high catalytic activity and high enantioselectivity. N-Methyl-N-phenyl allylic amines were indispensable to achieve the high catalytic activity, to achieve the high enantioselectivity, and to expand the substrate scope to 5- and 7-membered beta-ketoesters, whose nickel-catalyzed AAA with allylic alcohols results in low enantioselectivity. On the basis of the kinetics using a catalyst system made of Ni(cod)(2) and (S)-Tol-MeO-BIPHEP, and DFT calculations for the reaction pathway of the AAA reaction mediated by an isolated olefin-coordinated nickel-DPPF complex 4b, we propose a mechanism where protonation of the nitrogen atom of the coordinating allylic amine by beta-ketoester is key to cleaving the C-N bond and delivering a cationic pi-allyl nickel(II) intermediate.
Shanghai Jiao Tong Univ
5/15/2020TRUEFALSETRUEyyCsp3-Csp3E-NuNH
N(Me)Ph
HAlkylAlkylNo baseNo BaseNi(0)/Ni(II)_X10.1021/acscatal.1c0162610.1002/ejic.202100820,10.1021/acs.orglett.1c02893,10.1021/acscatal.1c03449,10.1021/acs.orglett.1c02406,10.1039/d1cc03292e,10.1021/acscatal.1c02790,10.1002/ejoc.202100642,10.1002/asia.202100432,10.1021/acscatal.1c01626,10.1002/ejoc.202100310,10.1021/acs.organomet.0c00789,10.1021/acs.chemrev.0c01115Long11/1/2021MAY 152020FALSEFALSEFALSEFALSE10105828
42
165FALSEanie.20150875710.1002/anie.201508757https://sci-hub.wf/10.1002/anie.201508757https://doi.org/10.1002/anie.201508757NiC-O ActivationLongTRUE897552016Mashima, K
Asymmetric Allylic Alkylation of -Ketoesters with Allylic Alcohols by a Nickel/Diphosphine Catalyst
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Asymmetric allylic alkylation of -ketoesters with allylic alcohols catalyzed by [Ni(cod)(2)]/(S)-H-8-BINAP was found to be a superior synthetic protocol for constructing quaternary chiral centers at the -position of -ketoesters. The reaction proceeded in high yield and with high enantioselectivity using various -ketoesters and allylic alcohols, without any additional activators. The versatility of this methodology for accessing useful and enantioenriched products was demonstrated.
Osaka Univ1/18/2016TRUEFALSEFALSEyCsp2_ar-Csp3E-NuOHOHHArylAlkylNo baseNo BaseStrong-0.81_xx10.1021/acscatal.1c01626,10.1039/c7sc03140h,10.1021/acs.joc.6b02564,10.1021/acscatal.0c01356,10.1002/anie.201703486,10.1039/c7sc05216b,10.1021/acscatal.7b0307910.1039/d1nj05143a,10.1021/acs.orglett.1c03933,10.1002/ejic.202100820,10.1002/chem.202103093,10.1021/acscatal.1c03729,10.1021/acs.organomet.1c00491,10.1021/acscatal.1c03732,10.1021/acscatal.1c03449,10.1002/anie.202108336,10.1021/acs.orglett.1c02406,10.1021/acs.orglett.1c01879,10.1021/acscatal.1c02790,10.1021/acs.chemrev.0c00564,10.1002/asia.202100432,10.1021/acs.orglett.1c01369,10.1021/acscatal.1c01626,10.1039/d1qo00490e,10.1039/d1qo00370d,10.1021/acs.chemrev.0c00736,10.1016/j.tetlet.2021.152916,10.1021/acs.chemrev.0c01115,10.1002/ejoc.202001306,10.6023/cjoc202005008,10.1021/acs.chemrev.9b00682,10.1021/acs.orglett.0c01747,10.1021/acscatal.0c01356,10.1039/d0dt00741b,10.1039/d0ra02912b,10.1016/j.jorganchem.2020.121199,10.1021/acs.orglett.0c00936,10.1021/acs.orglett.0c01109,10.1021/acs.joc.0c00008,10.1021/acs.joc.0c00094,10.1039/c9cc09899b,10.1002/anie.202000704,10.1039/c9gc03619a,10.1021/acs.orglett.9b03730,10.1016/j.mencom.2020.01.010,10.1021/acs.orglett.9b03633,10.1039/c9fd00041k,10.1021/acs.joc.9b02282,10.1021/jacs.9b08734,10.1021/acs.joc.9b01293,10.1021/acs.joc.9b00616,10.1039/c9dt00443b,10.1002/chem.201805987,10.1002/adsc.201801351,10.1021/acs.orglett.8b04030,10.1021/acs.chemrev.8b00506,10.6023/cjoc201809037,10.1002/anie.201809112,10.6023/A18060224,10.1039/c8qo00827b,10.1002/cjoc.201800237,10.1021/acs.orglett.8b02188,10.1002/chem.201800348,10.1002/chem.201801241,10.1002/adsc.201800187,10.1039/c7sc05216b,10.1002/chem.201705164,10.1039/c7sc03140h,10.1055/s-0036-1590869,10.1021/acscatal.7b03079,10.1002/cjoc.201700596,10.1021/acs.orglett.7b03023,10.1039/c7cc05595a,10.1002/anie.201703380,10.1002/anie.201703486,10.1021/acs.joc.7b00657,10.1021/acs.orglett.7b01336,10.1021/acs.orglett.7b01208,10.1002/anie.201702857,10.6023/cjoc201702013,10.1021/acs.joc.6b02564,10.1021/acscatal.6b03631,10.1002/anie.201609693,10.1002/anie.201608752,10.1016/j.ica.2016.07.048,10.1002/ejoc.201600677,10.1002/ejoc.201600500,10.1055/s-0035-1560396,10.1002/ejoc.201501556Kelly1/4/2022JAN 182016FALSEFALSEFALSEFALSE5531098
43
46FALSEacscatal.0c0039310.1021/acscatal.0c00393https://sci-hub.wf/10.1021/acscatal.0c00393https://doi.org/10.1021/acscatal.0c00393NiC-H ActivationGerryTRUE181302020Morandi, B
Nickel-Catalyzed Amination of Aryl Thioethers: A Combined Synthetic and Mechanistic StudyACS CATAL
Herein, we report a nickel-1,2-bis-(dicyclohexylphosphino)ethane (dcype) complex for the catalytic Buchwald-Hartwig amination of aryl thioethers. The protocol shows broad applicability with a variety of different functional groups tolerated under the catalytic conditions. Extensive organo-metallic and kinetic studies support a nickel(0)-nickel(II) pathway for this transformation and revealed the oxidative addition complex as the resting state of the catalytic cycle. All the isolated intermediates have proven to be catalytically and kinetically competent catalysts for this transformation. The fleeting transmetalation intermediate has been successfully synthesized through an alternative synthetic organometallic pathway at lower temperature, allowing for in situ NMR study of the C-N bond reductive elimination step. This study addresses key factors governing the mechanism of the nickel-catalyzed Buchwald-Hartwig amination process, thus improving the understanding of this important class of reactions.
Swiss Fed Inst Technol
4/17/2020TRUEFALSETRUEyNsp3-Csp2_arE-NuSHSMeH
Morpholine
ArylLiHMDSIonicNitrogen(neutral)_xxx10.1002/anie.20220035210.1039/d2cp00105e,10.1002/anie.202200352,10.1021/acscatal.1c05386,10.1021/acscatal.1c05386,10.1002/hlca.202100177,10.1016/j.tet.2021.132453,10.1021/acs.orglett.1c02285,10.1021/jacs.1c03763,10.1002/chem.202101273,10.1021/jacs.1c04215,10.1016/j.xcrp.2021.100462,10.1021/acs.joc.1c00681,10.1002/chem.202100342,10.1021/acs.organomet.1c00078,10.1111/cote.12536,10.1021/jacs.1c0052911/1/2021APR 172020FALSEFALSEFALSEFALSE1084630
44
190FALSEanie.20151049710.1002/anie.201510497https://sci-hub.wf/10.1002/anie.201510497https://doi.org/10.1002/anie.201510497NiC-O ActivationShihongTRUE10421892016Rueping, M
Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C-O Bond-Cleaving Alkylation: Prevention of Undesired -Hydride Elimination
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
In the presence of trialkylaluminum reagents, diverse aryl methyl ethers can be transformed into valuable products by C-O bond-cleaving alkylation, for the first time without the limiting -hydride elimination. This new nickel-catalyzed dealkoxylative alkylation method enables powerful orthogonal synthetic strategies for the transformation of a variety of naturally occurring and easily accessible anisole derivatives. The directing and/or activating properties of aromatic methoxy groups are utilized first, before they are replaced by alkyl chains in a subsequent coupling process.
Rhein Westfal TH Aachen
5/10/2016TRUETRUEFALSECsp2_ar-Csp3E-NuOAlOMeAlMe2ArylAlkylNo baseNo BaseStrong-0.28_10.1016/j.tet.2017.06.004,10.1055/s-0036-1590863,10.1002/anie.201806790,10.1021/acs.orglett.7b00556,10.1021/jacs.1c09797,10.1021/jacs.7b04973,10.1021/jacs.7b02326,10.1039/c9sc00783k,10.1021/acscatal.7b01058,10.1021/acscatal.8b03436,10.1021/jacs.7b04279,10.1002/anie.202004116,10.1002/chem.201702867,10.1021/acs.orglett.8b01021,10.1021/acscatal.7b00941,10.1002/chem.201603436,10.1021/jacs.9b00097,10.1021/jacs.6b03253,10.1021/acscatal.6b00801,10.1021/jacs.7b12865,10.1002/anie.20160764610.1021/acs.organomet.1c00578,10.1039/d1qo01580j,10.1021/jacs.1c09797,10.1002/anie.202110785,10.1039/d1cc05408b,10.1039/d1ob00955a,10.1039/d1qo00811k,10.1039/d1qo00549a,10.1002/anie.202104050,10.1039/d1cy00660f,10.1055/a-1509-5954,10.1021/jacs.1c03038,10.1039/d1qo00358e,10.1021/acs.accounts.1c00050,10.1021/acs.orglett.1c00280,10.6023/cjoc202006077,10.1021/acs.orglett.0c03507,10.1039/d0ob01815e,10.1021/acs.chemrev.0c00088,10.1002/cssc.202000978,10.1002/asia.202000763,10.1021/acs.orglett.0c02609,10.1021/acs.orglett.0c02236,10.1021/acs.chemrev.9b00682,10.1002/anie.202004116,10.1039/d0sc01585g,10.1021/acs.organomet.0c00338,10.1021/acs.joc.0c00640,10.1002/cjoc.201900506,10.1002/cssc.201903397,10.1039/c9qo01428d,10.1002/jccs.201900450,10.1002/chem.201904842,10.1021/acscatal.9b02636,10.1002/cctc.201900047,10.1039/c9nj01748h,10.1016/j.tet.2019.03.010,10.1039/c9dt00455f,10.1039/c9sc00783k,10.1021/jacs.9b00097,10.1021/jacs.8b13884,10.1007/3418_2018_19,10.1016/j.apsusc.2018.08.241,10.1021/acscatal.8b03436,10.1055/s-0037-1609941,10.1021/acs.orglett.8b02351,10.1002/anie.201806790,10.1021/acs.orglett.8b01696,10.1002/chem.201704670,10.1016/j.jorganchem.2018.01.019,10.1021/acs.orglett.8b01021,10.1021/acs.orglett.8b01233,10.1021/acs.accounts.8b00023,10.1021/acs.orglett.8b00847,10.1021/acs.joc.8b00027,10.1021/acscatal.8b00230,10.1021/jacs.7b12865,10.1002/cjoc.201700664,10.1039/c7cc08709h,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.1002/chem.201703266,10.1055/s-0036-1590863,10.1055/s-0036-1588568,10.1055/s-0036-1591495,10.1002/anie.201708573,10.1021/jacs.7b04973,10.1002/chem.201702867,10.1248/cpb.c17-00487,10.1021/acs.orglett.7b01905,10.1021/jacs.7b04279,10.1016/j.tet.2017.06.004,10.1021/acscatal.7b00941,10.1021/acscatal.7b01058,10.1021/jacs.7b02326,10.1021/jacs.7b02742,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1002/anie.201612624,10.1002/adsc.201601105,10.1021/acs.orglett.6b03861,10.1021/acscatal.6b03344,10.1021/acs.organomet.6b00769,10.1021/jacs.6b10998,10.1021/acscatal.6b02964,10.1002/anie.201607646,10.1002/chem.201604160,10.1002/chem.201604452,10.1002/chem.201604504,10.1002/chem.201603436,10.1021/acs.organomet.6b00638,10.1002/asia.201600972,10.1002/anie.201604696,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1021/jacs.6b03253,10.1016/bs.adomc.2016.07.001 Long 11/5/2021MAY 102016FALSEFALSEFALSEFALSE55206093
45
287FALSEanie.20151143810.1002/anie.201511438https://sci-hub.wf/10.1002/anie.201511438https://doi.org/10.1002/anie.201511438NiC-O ActivationxJustin29-MayTRUE1551452016Doyle, AG
Direct Acylation of C(sp(3))-H Bonds Enabled by Nickel and Photoredox Catalysis
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Using nickel and photoredox catalysis, the direct functionalization of C(sp(3))-H bonds of N-aryl amines by acyl electrophiles is described. The method affords a diverse range of -amino ketones at room temperature and is amenable to late-stage coupling of complex and biologically relevant groups. C(sp(3))-H activation occurs by photoredox-mediated oxidation to generate -amino radicals which are intercepted by nickel in catalytic C(sp(3))-C coupling. The merger of these two modes of catalysis leverages nickel's unique properties in alkyl cross-coupling while avoiding limitations commonly associated with transition-metal-mediated C(sp(3))-H activation, including requirements for chelating directing groups and high reaction temperatures.
3/14/2016Csp2-Csp3E-NuOHOC(O)H
Carbonyl
AlkylNo baseNo Base6/15/2022
46
199FALSEanie.20151148610.1002/anie.201511486https://sci-hub.wf/10.1002/anie.201511486https://doi.org/10.1002/anie.201511486NiC-O ActivationLongTRUE11312542016Garg, NK
Nickel-Catalyzed Activation of Acyl C-O Bonds of Methyl Esters
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
We report the first catalytic method for activating the acyl C-O bonds of methyl esters through an oxidative-addition process. The oxidative-addition adducts, formed using nickel catalysis, undergo in situ trapping to provide anilide products. DFT calculations are used to support the proposed reaction mechanism, to understand why decarbonylation does not occur competitively, and to elucidate the beneficial role of the substrate structure and the Al(OtBu)(3) additive on the kinetics and thermodynamics of the reaction.
Univ Calif Los Angeles
2/18/2016TRUEFALSEFALSECsp2-Nsp3E-NuOHOMeH
Carbonyl
N(Alkyl)Aryl
Al(OtBu)3Ionic-OtBuStrong-0.28_xxx10.1002/chem.201702867,10.1021/acscatal.7b00941,10.1021/acscatal.6b00793,10.1002/chem.201605095,10.1021/jacs.7b06191,10.1038/ncomms14878,10.1039/c7cc06717h,10.1021/acscatal.9b00884,10.1021/acscatal.7b03688,10.1021/acs.orglett.7b00660,10.1002/anie.202103327,10.1002/anie.20180856010.1021/acs.jpcc.1c09050,10.1021/acs.inorgchem.1c02127,10.1021/acs.jpca.1c05412,10.1002/tcr.202100224,10.1039/d1ob01409a,10.1039/d1ra04651a,10.1039/d1sc02210e,10.1039/d1cy00660f,10.1002/anie.202103327,10.1039/d1gc00720c,10.1021/acs.orglett.1c00940,10.1126/science.abg5526,10.1039/d1ob00187f,10.1039/d0cc08389e,10.1246/bcsj.20200277,10.1021/acssuschemeng.0c08262,10.1021/acs.joc.0c02478,10.1002/pep2.24210,10.1002/adsc.202000794,10.1021/acscatal.0c03334,10.1002/anie.202008350,10.1055/s-0040-1707101,10.1039/d0ob01083a,10.1002/ejoc.202000575,10.1039/d0ob00789g,10.1021/jacs.0c02405,10.1021/jacs.0c02839,10.1021/acscatal.9b05049,10.1039/c9gc03608c,10.1038/s41467-020-14799-8,10.3390/catal10020230,10.1002/aoc.5517,10.1039/c9cc07710c,10.1002/anie.201911372,10.1002/aoc.5181,10.3390/catal9100840,10.1021/acscatal.9b02641,10.1021/acscatal.9b00884,10.1039/c8qo01405a,10.1021/acs.orglett.9b00554,10.1039/c8qo01052h,10.1055/s-0037-1610664,10.1038/s41929-018-0215-1,10.1055/s-0037-1610267,10.1021/acs.organomet.8b00720,10.1002/slct.201803105,10.1016/j.jorganchem.2018.09.026,10.1038/s41557-018-0110-z,10.1039/c8qo00591e,10.3390/molecules23102681,10.1002/anie.201808560,10.1002/ejoc.201800253,10.1002/cctc.201800609,10.1002/asia.201800478,10.1038/s41467-018-06019-1,10.1021/acs.joc.8b00819,10.1039/c8ob01034j,10.1039/c8cc03823f,10.1021/acs.orglett.8b01646,10.1002/chem.201704670,10.1016/j.jorganchem.2018.01.019,10.1021/acs.orglett.8b01233,10.1021/acs.organomet.8b00011,10.1016/j.jorganchem.2018.02.023,10.1002/ajoc.201800070,10.1021/acs.orglett.8b00080,10.1021/acscatal.7b03688,10.1021/acs.orglett.7b03669,10.1021/acs.joc.7b02588,10.1021/acsomega.7b01540,10.1039/c7cc06717h,10.1055/s-0036-1589120,10.1039/c7nj02488f,10.1039/c7cs00182g,10.1002/chem.201702867,10.1039/c7sc02692g,10.1021/jacs.7b06191,10.1039/c7cc04252c,10.1002/chem.201702608,10.1002/asia.201700313,10.1021/acscatal.7b00941,10.1039/c7qo00068e,10.1038/ncomms14993,10.1039/c7ob00593h,10.1021/acs.organomet.7b00208,10.1021/acs.orglett.7b00494,10.1021/acs.orglett.7b00660,10.1021/acs.orglett.7b00429,10.1021/acs.orglett.7b00579,10.1002/anie.201611819,10.1002/anie.201612624,10.1038/ncomms14878,10.1002/ajoc.201600596,10.1021/acscatal.7b00245,10.1021/acscatal.6b03277,10.1021/jacs.6b12329,10.1021/acscatal.6b03040,10.1002/chem.201605095,10.1021/acs.joc.6b02093,10.1002/chem.201604504,10.1021/acscatal.6b01956,10.1002/anie.201604696,10.1002/anie.201603399,10.1002/anie.201603068,10.1021/acscatal.6b00793Kelly11/16/2021FEB 182016FALSEFALSEFALSEFALSE5582810
47
140FALSEanie.20160120610.1002/anie.201601206https://sci-hub.wf/10.1002/anie.201601206https://doi.org/10.1002/anie.201601206NiC-O ActivationGerryTRUE727322016Jarvo, ER
Intra- and Intermolecular Nickel-Catalyzed Reductive Cross-Electrophile Coupling Reactions of Benzylic Esters with Aryl Halides
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Nickel-catalyzed cross-electrophile coupling reactions of benzylic esters and aryl halides have been developed. Both inter-and intramolecular variants proceed under mild reaction conditions. A range of heterocycles and functional groups are tolerated under the reaction conditions. Additionally, the first example of a stereospecific cross-electrophile coupling of a secondary benzylic ester is described.
Univ Calif Irvine6/1/2016TRUETRUEFALSECsp3-Csp2_arE-NuOHOPivHAlkylArylNo baseNo BaseMedium0.33_xx10.1002/anie.201805611,10.1021/jacs.0c13093,10.1039/c8sc00609a,10.1021/jacs.0c12462,10.1021/jacs.9b05224,10.1021/jacs.0c01330,10.1021/acs.orglett.9b0017410.1002/anie.202201370,10.1002/cjoc.202100819,10.1055/s-0041-1737762,10.1021/acscatal.1c05144,10.1021/jacs.1c10932,10.6023/cjoc202106021,10.1021/acscatal.1c04143,10.1021/acs.orglett.1c02893,10.1021/acs.orglett.1c03210,10.1021/acscatal.1c02307,10.1021/jacs.1c08695,10.1021/jacs.0c13093,10.1021/acs.orglett.0c04316,10.1021/jacs.0c12462,10.1007/s11426-020-9910-2,10.1021/jacs.0c09922,10.1055/s-0040-1705987,10.7536/PC200607,10.1038/s41467-020-19717-6,10.1021/acscatal.0c03237,10.1021/acscatal.0c01842,10.1021/jacs.0c05254,10.1021/acs.orglett.0c01284,10.1021/acs.orglett.0c00554,10.1016/j.chempr.2020.01.009,10.1021/jacs.0c01475,10.1021/jacs.0c01330,10.1016/j.chempr.2019.12.026,10.1021/acscatal.9b02636,10.1021/jacs.9b02973,10.1016/j.tetlet.2019.150991,10.1021/jacs.9b05224,10.1039/c9ob00628a,10.1021/acs.orglett.9b00174,10.6023/cjoc201806038,10.1002/ejoc.201801690,10.1039/c8sc04335c,10.1002/chem.201805682,10.1021/acs.organomet.8b00720,10.1039/c8qo01044g,10.1021/acscatal.8b03930,10.1039/c8dt03188f,10.1039/c8cc07093h,10.1021/acscatal.8b02784,10.1002/adsc.201800468,10.1002/anie.201805611,10.1002/chem.201801241,10.1039/c8sc00609a,10.1021/acs.orglett.8b00408,10.1039/c8cc00001h,10.1021/acs.orglett.8b00114,10.1055/s-0036-1591853,10.1021/acscatal.7b03432,10.1021/acs.orglett.7b03049,10.1055/s-0036-1590962,10.1021/jacs.7b06469,10.1038/s41570-017-0065,10.1021/acs.orglett.7b01135,10.1021/jacs.7b03195,10.1021/jacs.7b02742,10.1002/chem.201605445,10.1002/anie.201607959,10.1055/s-0035-1560565,10.1021/jacs.6b09533,10.1021/acs.orglett.6b02665,10.1007/s41061-016-0042-2,10.1021/jacs.6b04566Kelly1/10/2022JUN 12016FALSEFALSEFALSEFALSE55236730
48
134FALSEanie.20160764610.1002/anie.201607646https://sci-hub.wf/10.1002/anie.201607646https://doi.org/10.1002/anie.201607646NiC-O ActivationKellyTRUE7113892016Rueping, M
Nickel-Catalyzed Alkoxy-Alkyl Interconversion with Alkylborane Reagents through C-O Bond Activation of Aryl and Enol Ethers
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
A nickel-catalyzed alkylation of polycyclic aromatic methyl ethers as well as methyl enol ethers with B-alkyl 9-BBN and trialkylborane reagents that involves the cleavage of stable C(sp(2))-OMe bonds is described. The transformation has a wide substrate scope and good chemoselectivity profile while proceeding under mild reaction conditions; it provides a versatile way to form C(sp(2))-C(sp(3)) bonds that does not suffer from -hydride elimination. Furthermore, a selective and sequential alkylation process by cleavage of inert C-O bonds is presented to demonstrate the advantage of this method.
Rhein Westfal TH Aachen
12/5/2016Csp2_ar-Csp3E-NuOBOMe9-BBNArylAlkylCsFIonic-FStrong-0.28_xx10.1021/acscatal.7b00941,10.1021/acs.orglett.8b01021,10.1021/acscatal.7b01058,10.1039/c9sc00783k,10.1021/jacs.8b02134,10.1021/jacs.7b12865,10.1021/jacs.7b04279,10.1021/jacs.1c09797,10.1021/jacs.7b02326,10.1021/acs.orglett.7b00556,10.1002/anie.201806790,10.1002/chem.201702867,10.1021/jacs.8b0877910.1039/d1qo01614h,10.1021/jacs.1c09797,10.1039/d1ob01503f,10.1002/anie.202106356,10.1039/d1qo00549a,10.6023/cjoc202006077,10.1021/acscatal.0c03771,10.1021/acs.orglett.0c03507,10.1021/acs.chemrev.0c00088,10.1021/acs.orglett.0c02236,10.1039/d0sc01641a,10.1021/acs.joc.0c00640,10.1021/jacs.0c02839,10.3390/catal10030296,10.1039/c9qo01428d,10.1039/c9cc07558e,10.1002/chem.201904842,10.1002/anie.201911372,10.1016/j.jcat.2019.07.026,10.1021/acs.oprd.9b00235,10.1039/c9nj01748h,10.1039/c9sc00783k,10.1002/chem.201900498,10.1007/3418_2018_19,10.1002/cjoc.201800500,10.1039/c8qo00729b,10.1021/jacs.8b08779,10.1021/acs.orglett.8b02351,10.1002/anie.201806790,10.1055/s-0037-1610023,10.1021/acs.orglett.8b01696,10.1021/jacs.8b04479,10.1002/chem.201704670,10.1021/acs.orglett.8b01021,10.1021/acs.accounts.8b00023,10.1021/acscatal.8b01224,10.1038/s41467-018-03928-z,10.1021/acs.organomet.8b00046,10.1021/jacs.8b02134,10.1055/s-0036-1591523,10.1021/jacs.7b12865,10.1039/c8cc00001h,10.1039/c7cc08709h,10.1039/c7cy01205e,10.1039/c7cc08416a,10.1002/chem.201703266,10.1055/s-0036-1588568,10.1055/s-0036-1591495,10.1055/s-0036-1590962,10.1021/acs.orglett.7b02166,10.1002/chem.201702867,10.1248/cpb.c17-00487,10.1021/acs.orglett.7b01905,10.1021/jacs.7b04279,10.1021/acscatal.7b00941,10.1021/acscatal.7b01058,10.1021/jacs.7b02326,10.1021/acs.organomet.7b00165,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1002/anie.201612624,10.1021/jacs.6b10998Kelly11/5/2021
49
53FALSEj.tet.2017.06.00410.1016/j.tet.2017.06.004https://sci-hub.wf/10.1016/j.tet.2017.06.004https://doi.org/10.1016/j.tet.2017.06.004NiC-N ActivationShihongTRUE16152017Wang, ZX
Nickel-catalyzed cross-coupling of aryl or 2-menaphthyl quaternary ammonium triflates with organoaluminum reagents
TETRAHEDRON
The cross-coupling of aryltrimethylammonium triflates with AIMe(3) and beta-H-containing trialkylaluminums was performed in dioxane at 110 C-omicron under catalysis of (dPPP)NiCl2 to afford alkylated arenes. The cross-coupling of 2-menaphthyltrimethylammonium triflate with trialkylaluminums and 1-naphthyltrimethylammonium triflate with triarylaluminums was also carried out respectively under the same conditions. (C) 2017 Elsevier Ltd. All rights reserved.
Univ Sci & Technol China
7/27/2017Csp2_ar-Csp3E-NuNAl
NMe3+OTf-
AlMe2ArylAlkylNo baseNo BaseE-H_10.1021/jacs.0c0467010.3390/molecules26195947,10.1016/j.tet.2021.132431,10.1039/d1ob01468d,10.1039/d1qo00759a,10.6023/cjoc202009029,10.1039/c9ob02667c,10.1039/c9ob02107h,10.1021/acs.orglett.9b02820,10.1021/acscatal.9b00218,10.1021/acs.joc.8b02926,10.1021/acsomega.8b02916,10.6023/cjoc201803013,10.1002/anie.201804628,10.1002/ajoc.201800264,10.1016/j.jorganchem.2018.01.020,10.6023/cjoc201709041Long12/22/2021
50
54FALSEanie.20171269310.1002/anie.201712693https://sci-hub.wf/10.1002/anie.201712693https://doi.org/10.1002/anie.201712693NiC-H ActivationLongTRUE191#N/A2018Ho, CY
(NHC)NiH-Catalyzed Regiodivergent Cross-Hydroalkenylation of Vinyl Ethers with -Olefins: Syntheses of 1,2-and 1,3-Disubstituted Allyl Ethers
ANGEW CHEM INT EDIT
Cross-hydroalkenylation of a vinyl ether (1) with an -olefin (2) was first achieved by a set of [NHC-Ni(allyl)]BArF (NHC=N-heterocyclic carbene) catalysts. Both 1,2- and 1,3-disubstituted allyl ethers were obtained, highly selectively, by using NHCs of different sizes. In contrast, the chemoselectivity (i.e., 1 as acceptor and 2 as donor) was controlled mostly by electronic effects through the catalyst-substrate interaction. Sterically bulkier alkenes (2) were used as preferred donors compared to smaller alkenes. This electronic effect also served as a basis for the first tail-to-head cross-hydroalkenylations of 1 with either a vinyl silane or boronic ester.
Southern Univ Sci & Technol SUSTech
3/1/2018TRUEFALSEFALSECsp2-Csp2Nu-NuHHHHVinylVinylNo baseNo BaseNu-H_xx10.1002/adsc.202100585,10.1016/j.jscs.2021.101260,10.1039/d1cc00709b,10.1021/jacs.1c02117,10.1016/j.eurpolymj.2020.110183,10.6023/cjoc202005050,10.1002/adsc.202000718,10.1021/jacs.0c04140,10.1038/s41467-020-16139-2,10.1002/anie.201914542,10.1021/acs.macromol.9b01484,10.1039/c8cs00872h,10.1002/anie.201904994,10.1039/c8cc10177a,10.1002/anie.201901255,10.1055/s-0037-1610410,10.1039/c8qo01020j,10.1002/cjoc.20180031411/1/2021MAR 12018FALSEFALSEFALSEFALSE57102677
51
295FALSEanie.20170009710.1002/anie.201700097https://sci-hub.wf/10.1002/anie.201700097https://doi.org/10.1002/anie.201700097NiC-O ActivationxWilliam11-JunTRUE791452017Doyle, AG
Dual Nickel- and Photoredox-Catalyzed Enantioselective Desymmetrization of Cyclic meso-Anhydrides
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
The enantioselective desymmetrization of cyclic meso-anhydrides with benzyl trifluoroborates under nickel-photoredox catalysis is described. The reaction tolerates a variety of sterically and electronically different trifluoroborates, as well as structurally unique cyclic anhydrides. The trans isomer of the keto-acid products is also observed at varying levels dependent on the trifluoroborate identity and relative catalyst loading. A mechanism involving decarbonylation and Ni-C bond homolysis of a Ni-II adduct is proposed. This feature allows access to a trans keto-acid as the major product in high enantioselectivity from a cis meso anhydride.
3/20/2022Osp2-Csp3-ring(s)E-NuOB
O(Ring-Opening)
BF3KORBenzylNo baseNo BaseWeak16/15/2022
52
56FALSEc6ob01299j10.1039/c6ob01299jhttps://sci-hub.wf/10.1039/c6ob01299jhttps://doi.org/10.1039/c6ob01299jNiC-N ActivationKellyTRUE20152016Wang, ZX
Nickel catalyzed alpha-arylation of ketones with aryltrimethylammonium triflates
ORG BIOMOL CHEM
Nickel-catalyzed alpha-arylation of ketones involving aromatic C-N cleavage has been accomplished. Inter-molecular coupling of aromatic ketones with a variety of aryltrimethylammonium triflates was achieved in the presence of Ni(COD)(2), IPr center dot HCl, and LiOBut, giving alpha-arylated ketones in reasonable to excellent yields.
Univ Sci & Technol China
7/18/2016TRUETRUEFALSECsp2_ar-Csp3E-NuNH
Triphenylpyridinium+BF4-
HArylAlkylNo baseNo Base_xshihong added10.1002/anie.20200682610.1039/d1ob02023d,10.1016/j.tet.2021.132431,10.1039/d1ob01468d,10.1039/d1cc00913c,10.1039/d0qi01411g,10.1021/acs.joc.0c02992,10.1002/anie.202006398,10.1002/anie.202006826,10.1016/j.tetlet.2020.151647,10.1039/c9ob02667c,10.1021/acs.orglett.9b02830,10.1021/acs.orglett.9b01628,10.1021/acscatal.9b00218,10.1021/acs.joc.8b02926,10.1055/s-0037-1609963,10.1002/adsc.201701596,10.1002/asia.201701342,10.1002/ijch.201700044,10.1002/asia.201701132Long11/10/2021
53
92FALSEanie.20170552110.1002/anie.201705521https://sci-hub.wf/10.1002/anie.201705521https://doi.org/10.1002/anie.201705521NiC-O ActivationShihongTRUE64412017Gong, HG
Nickel-Catalyzed Reductive Allylation of Tertiary Alkyl Halides with Allylic Carbonates
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
The construction of all C(sp(3)) quaternary centers has been successfully achieved under Ni-catalyzed cross-electrophile coupling of allylic carbonates with unactivated tertiary alkyl halides. For allylic carbonates bearing C1 or C3 substituents, the reaction affords excellent regioselectivity through the addition of alkyl groups to the unsubstituted allylic carbon terminus. The allylic alkylation method also exhibits excellent functional-group compatibility, and delivers the products with high Eselectivity.
Shanghai Univ10/9/2017TRUETRUEFALSECsp3-Csp3E-EOX
OCO2Me
BrAllylAlkylpyridine-2,6-diamineNitrogenNitrogen(neutral)Medium0.31_xxx10.1021/jacs.8b12801,10.1021/jacs.0c12462,10.1039/c8sc00609a,10.1021/acs.orglett.8b0336710.1039/d1sc05605k,10.1055/s-0040-1719856,10.1016/j.chempr.2021.10.015,10.6023/cjoc202106021,10.1021/acscatal.1c02307,10.1021/acs.orglett.1c02938,10.1021/acs.orglett.1c02616,10.1021/jacs.1c06271,10.1039/d1sc02547c,10.1021/acscatal.1c01416,10.1021/acscatal.1c00225,10.1039/d1sc01115d,10.1039/d1qo00264c,10.1039/d0cs01107j,10.1021/acs.orglett.1c00431,10.6023/cjoc202008012,10.1021/jacs.0c12462,10.1055/a-1328-0352,10.1039/d0sc03217d,10.1038/s41467-020-18658-4,10.1021/acs.accounts.0c00291,10.1039/d0cs00262c,10.1039/d0cc00457j,10.1021/jacs.0c03239,10.1002/anie.201915454,10.1021/acs.orglett.0c00561,10.1039/c9cc07072a,10.2174/1385272824999200608135840,10.1021/acs.joc.9b02431,10.1002/asia.201901490,10.1002/anie.201909543,10.1002/anie.201909852,10.1021/acs.orglett.9b02473,10.1039/c9cc00768g,10.1021/jacs.9b02844,10.1021/acsomega.9b00163,10.1002/chem.201805682,10.1021/jacs.8b12801,10.1021/acs.orglett.8b03367,10.1039/c8cc07781a,10.1002/anie.201809919,10.1021/jacs.8b09473,10.1021/acs.orglett.8b02771,10.1016/j.tet.2018.07.057,10.1039/c8sc00609a,10.1021/acs.orglett.8b00408,10.1021/acs.orglett.8b00108,10.1021/acs.orglett.8b0011411/5/2021OCT 92017FALSEFALSEFALSEFALSE564213103
54
63FALSEanie.20171024110.1002/anie.201710241https://sci-hub.wf/10.1002/anie.201710241https://doi.org/10.1002/anie.201710241NiC-O ActivationShihongTRUE413152017Newman, SG
A Nickel-Catalyzed Carbonyl-Heck Reaction
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
The use of transition-metal catalysis to enable the coupling of readily available organic molecules has greatly enhanced the ability of chemists to access complex chemical structures. In this work, an intermolecular coupling reaction that unites organotriflates and aldehydes is presented. A unique catalyst system is identified to enable this reaction, featuring a Ni-0 precatalyst, a tridentate Triphos ligand, and a bulky amine base. This transformation provides access to a variety of ketone-containing products without the selectivity- and reactivity-related challenges associated with more traditional Friedel-Crafts reactions. A Heck-type mechanism is postulated, wherein the bond of the aldehyde takes the role of the olefin in the insertion/elimination steps.
Univ Ottawa11/27/2017TRUETRUETRUECsp2-Csp2E-NuOHOTfH
Carbonyl
Carbonyl
No baseNo BaseWeak0.53_xxx10.1002/anie.202002271,10.1021/jacs.9b03280,10.1021/acs.orglett.8b0102110.1002/anie.202201370,10.1039/d1ob02360h,10.1002/chem.202103653,10.1002/slct.202103003,10.1016/j.mcat.2021.111987,10.1021/jacs.1c05661,10.1021/jacs.1c07851,10.1021/jacs.1c07230,10.1021/acscatal.1c00951,10.1039/d1qo00487e,10.1039/d0nj06208a,10.1039/d0cc08389e,10.1039/d0ob01458c,10.1002/adsc.202000820,10.1021/acs.orglett.0c02909,10.1021/acs.orglett.0c02462,10.1002/anie.202006489,10.1021/acscatal.0c02105,10.1002/anie.202002271,10.1016/j.tet.2020.131201,10.1021/acs.orglett.0c01121,10.1038/s42004-020-0304-3,10.1002/chem.201903668,10.1021/acs.orglett.9b02788,10.1039/c9cc04726c,10.1021/acs.orglett.9b01782,10.1002/anie.201812534,10.1002/anie.201903330,10.1021/acs.orglett.9b00600,10.1021/jacs.9b03113,10.1021/jacs.9b03280,10.7536/PC181037,10.1039/c8cc06202a,10.1055/s-0037-1610161,10.1021/jacs.8b06966,10.1021/acscatal.8b01380,10.1021/acs.orglett.8b01021,10.1021/acscatal.8b0044011/5/2021NOV 272017FALSEFALSEFALSEFALSE564815441
55
288FALSEanie.20180070110.1002/anie.201800701https://sci-hub.wf/10.1002/anie.201800701https://doi.org/10.1002/anie.201800701NiC-O ActivationxJustin29-MayTRUE891852018Molander, GA
Synthesis of Reversed C-Acyl Glycosides through Ni/Photoredox Dual Catalysis
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
The incorporation of C-glycosides in drug design has become a routine practice for medicinal chemists. These naturally occurring building blocks exhibit attractive pharmaceutical profiles, and have become an important target of synthetic efforts in recent decades.([1]) Described herein is a practical, scalable, and versatile route for the synthesis of non-anomeric and unexploited C-acyl glycosides through a Ni/photoredox dual catalytic system. By utilizing an organic photocatalyst, a range of glycosyl-based radicals are generated and efficiently coupled with highly functionalized carboxylic acids at room temperature. Distinctive features of this transformation include its mild conditions, impressive compatibility with a wide array of functional groups, and most significantly, preservation of the anomeric carbon: a handle for further, late-stage derivatization.
5/28/2018Csp3-Csp3E-NuOCsp3OHDHPAlkylAlkylNo baseNo BaseStrong-0.816/15/2022
56
4FALSEanie.20180561110.1002/anie.201805611https://sci-hub.wf/10.1002/anie.201805611https://doi.org/10.1002/anie.201805611NiC-O ActivationGerryTRUE251272018Sweeney, JB
A Simple, Broad-Scope Nickel(0) Precatalyst System for the Direct Amination of Allyl Alcohols
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
The preparation of allylic amines is traditionally accomplished by reactions of amines with reactive electrophiles, such as allylic halides, sulfonates, or oxyphosphonium species; such methods involve hazardous reagents, generate stoichiometric waste streams, and often suffer from side reactions (such as overalkylation). We report here the first broad-scope nickel-catalysed direct amination of allyl alcohols: An inexpensive Ni-II/Zn couple enables the allylation of primary, secondary, and electron-deficient amines without the need for glove-box techniques. Under mild conditions, primary and secondary aliphatic amines react smoothly with a range of allyl alcohols, giving secondary and tertiary amines efficiently. This totally catalytic method can also be applied to electron-deficient nitrogen nucleophiles; the practicality of the process was demonstrated in an efficient, gram-scale preparation of the calcium antagonist drug substance flunarizine (Sibelium (R)).
Univ Lancaster8/6/2018TRUEFALSEFALSECsp3-Nsp3E-NuOHOHHAllyl
N(Alkyl)Alkyl
NitrogenNitrogen(charged)Strong-0.81_x10.1021/acscatal.0c0135610.1039/d1qo01530c,10.1002/ejic.202100820,10.1021/acscatal.1c03729,10.6023/cjoc202104030,10.1126/sciadv.abh4088,10.1021/acssuschemeng.0c08262,10.1002/ajoc.202000485,10.1016/j.jorganchem.2020.121373,10.1021/acs.chemrev.9b00682,10.1021/acscatal.0c01356,10.1039/d0sc01084g,10.1021/acs.orglett.0c00936,10.1002/anie.202000704,10.1021/acs.joc.9b02816,10.1021/acs.orglett.9b03633,10.1021/acs.orglett.9b02779,10.1021/acscatal.9b03038,10.1002/cssc.201900433,10.1002/adsc.2018013512/22/2022AUG 62018FALSEFALSEFALSEFALSE573210202
57
29FALSEanie.20180679010.1002/anie.201806790https://sci-hub.wf/10.1002/anie.201806790https://doi.org/10.1002/anie.201806790NiC-O ActivationKellyTRUE202162018
Montgomery, J
Nickel-Catalyzed Amination of Silyloxyarenes through C-O Bond Activation
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Silyloxyarenes were utilized as electrophilic coupling partners with amines in the synthesis of aniline derivatives. A diverse range of amine substrates were used, including cyclic or acyclic secondary amines, secondary anilines, and sterically hindered primary anilines. Additionally, a range of sterically hindered and unhindered primary aliphatic amines were employed, which have previously been challenging with other classes of aryl ether electrophiles. Orthogonal couplings of silyloxyarenes with aryl methyl ethers are illustrated, where selectivity between the two C-O electrophiles is determined by ligand control, thereby allowing complementary and selective late-stage diversification of either electrophile. Finally, a sequential coupling displays the utility of this amination method along with the reversal in intrinsic reactivity between aryl methyl ethers and silyloxyarenes.
Univ Michigan8/20/2018TRUETRUEFALSECsp2_ar-Nsp3E-NuOH
OSi(tBu)Me2
HAryl
Morpholine
No baseNo BaseStrong-0.27_x10.1021/jacs.0c00286,10.1021/jacs.1c0979710.1002/adsc.202101469,10.1021/jacs.1c09797,10.1002/anie.202103803,10.1021/acs.orglett.1c01280,10.1055/a-1337-5153,10.1038/s41467-020-19944-x,10.1002/cjoc.202000319,10.1021/acs.chemrev.0c00088,10.1002/chem.202002800,10.1021/jacs.0c00286,10.1002/adma.201906015,10.1002/anie.201904795,10.1039/c9sc01083a,10.1002/anie.201900659,10.1002/anie.201812862,10.1007/3418_2018_1911/4/2021AUG 202018FALSEFALSEFALSEFALSE573411045
58
62FALSEacscatal.6b0036510.1021/acscatal.6b00365https://sci-hub.wf/10.1021/acscatal.6b00365https://doi.org/10.1021/acscatal.6b00365NiC-H ActivationKellyTRUE611#N/A2016Stanley, LM
Coupling Catalytic Alkene Hydroacylation and alpha-Arylation: Enantioselective Synthesis of Heterocyclic Ketones with alpha-Chiral Quaternary StereocentersACS CATAL
We report a strategy that combines alkene hydroacylation and enantioselective alpha-(hetero)arylation reactions to form a wide variety of nitrogen-containing heterocyclic ketones bearing alpha-chiral quaternary stereogenic centers. Exo-selective, intramolecular Ni-catalyzed hydroacylations of N-homoallylindole- and N-homoallylpyrrole-2-carboxaldehydes form alpha-substituted six-membered heterocyclic ketones in up to 95% yield, while N-heterocyclic carbene (NHC) catalyzed hydroacylations of N-allylindole- and N-allylpyrrole-2-carboxaldehydes form alpha-substituted five-membered heterocyclic ketones in up to 99% yield. The racemic five- and six-membered products of Ni- and NHC-catalyzed hydroacylation reactions are readily transformed into heterocyclic ketones containing an alpha-chiral quaternary stereogenic center by enantioselective Ni-catalyzed alpha-arylation and alpha-heteroarylation reactions. The chiral, nonracemic products formed through a combination of alkene hydroacylation and alpha-(hetero)arylation reactions are formed in moderate to high yields (4499%) with excellent enantioselectivities (typically >95% ee). The identity of the precatalyst for Ni-catalyzed alpha-(hetero)arylation is dictated by the identity of the alpha-substituted heterocyclic ketone starting material. alpha-(Hetero)arylations of six-membered heterocyclic ketones occur at 65-85 C in the presence of a catalyst generated in situ from Ni(COD)(2) and (R)-BINAP or (R)-DIFLUORPHOS. alpha-(Hetero)arylation of five-membered heterocyclic ketones must be conducted at room temperature in the presence of an [((R)-BINAP)Ni(eta(2)-NC-Ph)] precatalyst or a catalyst generated in situ from Ni(COD)(2), (R)-DIFLUORPHOS, and benzonitrile.
Iowa State Univ4/1/2016TRUEFALSEFALSECsp3-Csp2_arE-NuXHBrHAlkylArylNaOtBuIonic-OtBu_x10.1021/jacs.0c0028610.1039/d1ob01103k,10.1002/slct.202100695,10.1016/j.chempr.2021.02.013,10.1021/acs.orglett.1c00470,10.1021/acs.chemrev.9b00682,10.1016/j.cclet.2019.09.008,10.1016/j.mcat.2019.110723,10.1021/acscatal.9b04480,10.1021/acs.orglett.9b01837,10.1021/acs.orglett.8b03767,10.1002/anie.201804318,10.1039/c8sc00827b,10.1021/acs.orglett.7b02732,10.1002/ejic.201700303,10.1002/asia.201601313,10.1021/jacs.6b11610,10.1002/ajoc.201600423,10.1002/chem.201603880,10.1021/acscatal.6b01852,10.1039/c6ob01956k11/2/2021APR2016FALSEFALSEFALSEFALSE642673
59
64FALSEacscatal.8b0426710.1021/acscatal.8b04267https://sci-hub.wf/10.1021/acscatal.8b04267https://doi.org/10.1021/acscatal.8b04267NiC-H ActivationElaineTRUE221#N/A2019Punji, B
Nickel-Catalyzed Straightforward and Regioselective C-H Alkenylation of Indoles with Alkenyl Bromides: Scope and Mechanistic AspectACS CATAL
Nickel-catalyzed regioselective C-H bond alkenylation of indoles and related heteroarenes with alkenyl bromides is accomplished under relatively mild conditions. This method allows the straightforward synthesis of C-2 alkenylated indoles employing an air-stable and well-defined nickel catalyst, (bpy)NiBr2, providing a solution to the limitations associated with hydroindolation and oxidative alkenylation. The reaction conceded the coupling of indole derivatives with various alkenyl bromides, such as aromatic and heteroaromatics, alpha- and beta-substituted as well as exo- and endo-cyclic alkenyl compounds. An extensive mechanistic investigation, including controlled study, reactivity experiments, kinetics and labeling studies, and EPR and XPS analyses, highlights that the alkenylation proceeds through a single-electron transfer process comprising an odd-electron oxidative addition of alkenyl bromide. Furthermore, the alkenylation operates via a probable Ni(I)/Ni(III) pathway involving the rate-limiting C-H nickelation of indole.
CSIR1/4/2019TRUETRUEFALSEhomobimetallic complexyyCsp2_ar-Csp2E-NuXHBrHHetVinylLiOtBuIonic-OtBu_10.1039/d2cy00027j,10.1002/asia.202101208,10.1021/acscatal.1c03314,10.7503/cjcu20210107,10.1002/cjoc.202100221,10.1039/d1nj01696b,10.1002/chem.202100468,10.1002/tcr.202100113,10.1002/adsc.202100116,10.1021/acs.orglett.1c00956,10.1039/d1ob00430a,10.1021/acscatal.0c05580,10.1039/d0qo01325k,10.1021/acssuschemeng.0c07465,10.1039/d0ob01265c,10.1021/acs.joc.0c00039,10.1002/cjoc.201900468,10.1002/ajoc.201900554,10.1021/acs.joc.9b01375,10.1002/adsc.201900586,10.1002/adsc.201900230,10.1016/j.trechm.2019.06.002,10.1002/chem.201900543,10.1039/c9ra03679b,10.1021/acs.organomet.9b0006012/15/2021JAN2019FALSEFALSEFALSEFALSE91431
60
85FALSEanie.20180856010.1002/anie.201808560https://sci-hub.wf/10.1002/anie.201808560https://doi.org/10.1002/anie.201808560NiC-O ActivationLongTRUE503152018Newman, SG
Nickel-Catalyzed Amide Bond Formation from Methyl Esters
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Despite being one of the most important and frequently run chemical reactions, the synthesis of amide bonds is accomplished primarily by wasteful methods that proceed by stoichiometric activation of one of the starting materials. We report a nickel-catalyzed procedure that can enable diverse amides to be synthesized from abundant methyl ester starting materials, producing only volatile alcohol as a stoichiometric waste product. In contrast to acid- and base-mediated amidations, the reaction is proposed to proceed by a neutral cross coupling-type mechanism, opening up new opportunities for direct, efficient, chemoselective synthesis.
Univ Ottawa9/24/2018TRUETRUEFALSECsp2-Nsp3E-NuOHOMeH
Carbonyl
Morpholine
No baseNo BaseStrong-0.28_10.1021/acscatal.9b00884,10.1002/anie.202012048,10.1002/anie.20210332710.1038/s41467-021-25836-5,10.1002/anie.202106412,10.3390/catal11080972,10.1039/d1ra04651a,10.1039/d1cc01795k,10.1055/a-1504-8366,10.1002/anie.202103327,10.6023/cjoc202009048,10.1002/chem.202100390,10.1039/d1gc00720c,10.1021/acs.orglett.1c00940,10.1039/d1ob00187f,10.1039/d0cc08389e,10.1246/bcsj.20200277,10.1002/adsc.202001496,10.1039/d0gc03912h,10.1021/acs.joc.0c02478,10.3390/molecules26010188,10.1002/anie.202012048,10.1002/pep2.24210,10.1021/acscatal.0c03334,10.1055/s-0040-1707101,10.1002/cctc.202001041,10.1039/d0sc01349h,10.1039/d0ob00789g,10.1021/jacs.0c02405,10.1021/jacs.9b13531,10.3390/molecules25051040,10.3390/catal10020229,10.1021/acs.orglett.9b04445,10.24820/ark.5550190.p011.417,10.1002/aoc.5323,10.1039/c9cc07710c,10.1002/anie.201911372,10.1039/c9cc05763c,10.1021/acs.orglett.9b02306,10.1021/acscatal.9b02641,10.1021/jacs.9b04136,10.1021/acscatal.9b00884,10.1039/c8qo01405a,10.1021/acs.orglett.9b00554,10.1002/anie.201813182,10.1021/acs.orglett.8b03542,10.1021/acs.organomet.8b00720,10.3390/molecules2310268111/9/2021SEP 242018FALSEFALSEFALSEFALSE573912925
61
66FALSEacs.joc.8b0249810.1021/acs.joc.8b02498https://sci-hub.wf/10.1021/acs.joc.8b02498https://doi.org/10.1021/acs.joc.8b02498NiDeletedWilliamFALSE271412018Liu, YH#N/ANickel-Catalyzed Cyanation of Phenol Derivatives with Zn(CN)(2) Involving C-O Bond CleavageJ ORG CHEM
An efficient nickel-catalyzed cyanation of aryl sulfonates, fluorosulfonates, and sulfamates with Zn(CN)(2) was developed, which provides a facile access to the nitrile products in generally good to excellent yields. The reaction is accomplished by using Ni-II complex as the precatalyst and DMAP as the additive. The method also displays wide functional group compatibility; for example, keto, methoxy, N,N-dimethylamino, cyano, ester, and pyridyl groups are well-tolerated during the reaction process.
Chinese Acad Sci11/16/2018_10.1055/a-1524-4912,10.1021/acscatal.1c01201,10.1039/d1qo00162k,10.2174/1570179418666210224124931,10.1021/acs.orglett.0c02722,10.1055/s-0040-1705943,10.1016/j.tet.2020.131388,10.1016/j.jorganchem.2020.121337,10.1021/acs.chemrev.9b00682,10.1021/acs.joc.0c00458,10.1039/d0ob00737d,10.1055/s-0040-1708007,10.1039/d0ra04629a,10.1002/ejoc.202000117,10.1021/acs.orglett.9b03170,10.1016/j.isci.2019.08.021,10.1016/j.tet.2019.130550,10.1002/anie.201906815,10.1002/adsc.201900813,10.1021/acs.joc.9b01103,10.1021/acs.orglett.9b02398,10.1021/acs.orglett.9b02621,10.1055/s-0037-1611793,10.1021/acs.joc.9b00151#N/A
62
67FALSEc9sc01446b10.1039/c9sc01446bhttps://sci-hub.wf/10.1039/c9sc01446bhttps://doi.org/10.1039/c9sc01446bNiC-H ActivationGerryTRUE281#N/A2019Punji, B
Nickel-catalyzed C-H alkylation of indoles with unactivated alkyl chlorides: evidence of a Ni(i)/Ni(iii) pathwayCHEM SCI
A mild and efficient nickel-catalyzed method for the coupling of unactivated primary and secondary alkyl chlorides with the C-H bond of indoles and pyrroles is described which demonstrates a high level of chemo and regioselectivity. The reaction tolerates numerous functionalities, such as halide, alkenyl, alkynyl, ether, thioether, furanyl, pyrrolyl, indolyl and carbazolyl groups including acyclic and cyclic alkyls under the reaction conditions. Mechanistic investigation highlights that the alkylation proceeds through a single-electron transfer (SET) process with Ni(i)-species being the active catalyst. Overall, the alkylation follows a Ni(i)/Ni(iii) pathway involving the rate-influencing two-step single-electron oxidative addition of alkyl chlorides.
NCL11/7/2019yCsp3-Csp2_arE-NuXHClHAlkylHetLiHMDSIonicNitrogen(neutral)_x10.1021/acscatal.0c0039310.1021/acscatal.1c05266,10.1039/d2cy00027j,10.1016/j.cclet.2021.06.091,10.1002/asia.202101208,10.1002/ajoc.202100515,10.1021/acscatal.1c03314,10.1055/a-1581-0934,10.1039/d1cc02798k,10.1021/jacs.1c03763,10.1039/d1nj01696b,10.1002/tcr.202100113,10.1021/acs.joc.1c00629,10.1002/adsc.202100116,10.1039/d0sc05409g,10.1021/acscatal.0c05580,10.1021/jacs.0c10882,10.1021/acs.joc.0c02069,10.1021/acssuschemeng.0c07465,10.1039/d0cc06652d,10.1038/s41929-020-00515-8,10.1021/acscatal.0c02030,10.1021/acs.orglett.0c01398,10.1002/anie.202004958,10.1039/d0gc00917b,10.1002/adsc.202000312,10.1021/acscatal.0c00393,10.1002/ajoc.2019005541/6/2022
63
68FALSEc6cc09685a10.1039/c6cc09685ahttps://sci-hub.wf/10.1039/c6cc09685ahttps://doi.org/10.1039/c6cc09685aNiDeletedGerryTRUE261462017Yu, DG
Coupling of C(sp(3))-H bonds with C(sp(2))-O electrophiles: mild, general and selective
CHEM COMMUN
Herein is reported the mild and general coupling of amine/ether C(sp(3))-H bonds with various kinds of C(sp(2))-O electrophiles with high selectivity and efficiency. Valuable allylic/benzylic amines are generated in moderate to excellent yields. The utility of this transformation is demonstrated by a broad substrate scope (> 50 examples), good functional group tolerance and facile product modification.
Sichuan Univ1/18/2017Csp2-Csp3E-NuOHOTsHVinylAlkylIonic-CO3Weak0.36_x10.1039/d1ra08568a,10.1021/acs.orglett.1c03500,10.3762/bjoc.17.143,10.1021/acs.orglett.1c00626,10.1021/acs.orglett.0c03703,10.7536/PC200607,10.1126/science.aba3823,10.1002/anie.201909543,10.1039/c9qo00092e,10.1080/00397911.2019.1582065,10.1039/c8sc05677c,10.1016/j.ica.2018.12.020,10.6023/cjoc201804012,10.1039/c8cc03604g,10.1055/s-0037-1610222,10.1039/c8qo00444g,10.1021/acs.orglett.8b01382,10.1002/ajoc.201700450,10.1021/acs.orglett.7b03551,10.1002/anie.201704513,10.1055/s-0036-1589126,10.1021/acs.orglett.7b03052,10.6023/cjoc201704051,10.1021/acs.orglett.7b01561,10.1002/ejoc.2017005142/14/2022
64
297FALSEanie.20180991910.1002/anie.201809919https://sci-hub.wf/10.1002/anie.201809919https://doi.org/10.1002/anie.201809919NiC-O ActivationxWilliam11-JunTRUE551852018Molander, GA
Photoredox/Nickel-Catalyzed Single-Electron Tsuji-Trost Reaction: Development and Mechanistic Insights
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
A regioselective, nickel-catalyzed photoredox allylation of secondary, benzyl, and alpha-alkoxy radical precursors is disclosed. Through this manifold, a variety of linear allylic alcohols and allylated monosaccharides are accessible in high yields under mild reaction conditions. Quantum mechanical calculations [DET and DLPNO-CCSD(T)/support the mechanistic hypothesis of a Ni-0 to Ni-11 oxidative addition pathway followed by radical addition and inner-sphere allylation.
11/26/2022Csp3-Csp3E-NuOB
O(Ring-Opening)
BF3KAlkylAlkylLutidine Weak16/15/2022
65
299FALSEanie.20190954310.1002/anie.201909543https://sci-hub.wf/10.1002/anie.201909543https://doi.org/10.1002/anie.201909543NiC-O ActivationxWilliam12-JunTRUE481#N/A2020Chu, LL
Visible-Light-Enabled Stereodivergent Synthesis of E- and Z-Configured 1,4-Dienes by Photoredox/Nickel Dual Catalysis
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
A stereodivergent reductive coupling reaction between allylic carbonates and vinyl triflates to furnish both E- and Z-configured 1,4-dienes has been achieved by visible-light-induced photoredox/nickel dual catalysis. The mild reaction conditions allow good compatibility of both vinyl triflates and allylic carbonates. Notably, the stereoselectivity of this synergistic cross-electrophile coupling can be tuned by an appropriate photocatalyst with a suitable triplet-state energy, providing a practical and stereodivergent means to alkene synthesis. Preliminary mechanistic studies shed some light on the coupling step as well as the control of the stereoselectivity step.
1/2/2022Csp2-Csp3E-EOOOTfOBocVinylAllylDABCONitrogenNitrogen(neutral)Weak0.536/15/2022
66
71FALSEjacs.7b0431210.1021/jacs.7b04312https://sci-hub.wf/10.1021/jacs.7b04312https://doi.org/10.1021/jacs.7b04312NiC-H ActivationGerryTRUE574#N/A2017Watson, DA
Nickel-Catalyzed C-Alkylation of Nitroalkanes with Unactivated Alkyl Iodides
J AM CHEM SOC
Enabled by nickel catalysis, a mild and general catalytic method for C-alkylation of nitroalkanes with unactivated alkyl iodides is described. Compatible with primary, secondary, and tertiary alkyl iodides; and tolerant of a wide range of functional groups, this method allows rapid access to diverse nitroalkanes.
Univ Delaware6/21/2017TRUEFALSEFALSECsp3-Csp3E-NuXHIHAlkylAlkylKOtBuIonic-OtBu_xxx10.1002/anie.202004116,10.1021/acscatal.8b03436,10.1021/jacs.8b02134,10.1021/acscatal.1c0480010.1002/ajoc.202100440,10.1039/d0cs01107j,10.7536/PC200607,10.1021/acs.inorgchem.0c00915,10.1002/slct.202002787,10.1021/acs.joc.0c00077,10.1021/acs.joc.0c00861,10.1021/acs.joc.9b03203,10.1021/acs.joc.9b03206,10.1002/anie.201913400,10.1038/s41467-019-14016-1,10.1021/acs.joc.9b01961,10.1021/acs.joc.9b02848,10.1021/acs.orglett.9b01898,10.1002/anie.201904034,10.1021/acs.orglett.9b01124,10.1021/jacs.9b04175,10.1038/s41467-018-07069-1,10.1039/c8ob01389f,10.1021/acs.joc.8b01372,10.1021/acs.organomet.8b00244,10.1021/acs.oprd.8b00113,10.1021/acscatal.7b03432,10.1246/cl.170798,10.1021/acscatal.7b0266311/15/2021JUN 212017FALSEFALSEFALSEFALSE139248110
67
72FALSEanie.20110209210.1002/anie.201102092https://sci-hub.wf/10.1002/anie.201102092https://doi.org/10.1002/anie.201102092NiC-H ActivationElaineTRUE302802011Itami, K
Controlled Alcohol-Carbonyl Interconversion by Nickel Catalysis
ANGEW CHEM INT EDIT
Nagoya Univ6/17/2011YCsp2_ar-Csp3-ring(s)Nu-NuBHB(nep)HArylBenzylCsFIonic-FNu-M_10.1021/jacs.1c06614,10.1021/jacs.9b0328010.1021/jacs.1c05661,10.1021/jacs.1c06614,10.1039/d0cc08389e,10.1002/cctc.202001464,10.1039/d0cc03966g,10.1002/cjoc.202000019,10.1021/acs.orglett.0c02340,10.1039/c9cc09497k,10.1021/acs.inorgchem.9b00784,10.1021/jacs.9b03280,10.1039/c8qo00729b,10.1038/s41467-018-04645-3,10.1016/j.tetlet.2018.03.026,10.1002/chem.201705577,10.1039/c6cc08759k,10.1021/acs.joc.6b02242,10.1021/acs.orglett.6b00932,10.1002/ejoc.201403634,10.1021/cs5014927,10.1021/ja500666h,10.1021/jo401217x,10.1002/ejoc.201300269,10.1002/adsc.201200108,10.1021/om201101g,10.1021/ol300275s,10.1021/om200864z,10.1246/cl.2011.114012/16/2021
68
284FALSEanie.20191016810.1002/anie.201910168https://sci-hub.wf/10.1002/anie.201910168https://doi.org/10.1002/anie.201910168NiC-O ActivationxJustin28-MayTRUE541#N/A2019Melchiorre, P
Photochemical Asymmetric Nickel-Catalyzed Acyl Cross-Coupling
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Photochemical enantioselective nickel-catalyzed cross-coupling reactions are difficult to implement. We report a visible-light-mediated strategy that successfully couples symmetrical anhydrides and 4-alkyl dihydropyridines (DHPs) to afford enantioenriched alpha-substituted ketones under mild conditions. The chemistry does not require exogenous photocatalysts. It is triggered by the direct excitation of DHPs, which act as a radical source and as a reductant, facilitating the turnover of the chiral catalytic nickel complex.
11/18/2019Csp2-Csp3E-NuOCsp3OC(O)DHP
Carbonyl
AlkylNo baseNo Base6/1/2022
69
74FALSEacscatal.7b0307910.1021/acscatal.7b03079https://sci-hub.wf/10.1021/acscatal.7b03079https://doi.org/10.1021/acscatal.7b03079NiDeletedWilliamFALSE1222162018Michaelis, DJ#N/ANickel-Catalyzed Suzuki Cross Couplings with Unprotected Allylic Alcohols Enabled by Bidentate N-Heterocyclic Carbene (NHC)/Phosphine LigandsACS CATAL
Cross couplings between simple allylic alcohols and aryl and vinyl boronic acids are efficiently catalyzed by nickel(0) catalysts and bidentate N-heterocyclic carbene/phosphine ligands. The bidentate nature of the ligand is shown to extend catalyst lifetime and enable high yields of the corresponding cross-coupling products. X-ray crystallography confirms the bidentate nature of the ligand scaffold. Multistep cross coupling-alkene/alkyne insertions reactions are also conducted and the bidentate nature of the substrate makes the pendant phosphine of the ligand unnecessary.
Brigham Young Univ1/5/2018TRUETRUEFALSETMxx10.1021/acscatal.0c01356,10.1021/acscatal.9b0088410.3390/molecules27010095,10.1002/ejic.202100820,10.1021/acscatal.1c03729,10.1021/acscatal.1c03449,10.1021/acscatal.1c01421,10.1021/acs.organomet.1c00033,10.1039/d1ob00362c,10.1002/aoc.6158,10.1002/anie.202006322,10.1016/j.jorganchem.2020.121311,10.1002/adsc.202000186,10.1021/acscatal.0c01356,10.1021/acs.orglett.0c01109,10.1016/j.tetlet.2020.151721,10.1016/j.tet.2020.130968,10.1055/s-0039-1690740,10.1002/anie.202000704,10.1016/j.ultsonch.2019.104746,10.1021/acs.orglett.9b03633,10.1021/acs.orglett.9b03760,10.1002/chem.201903625,10.1039/c9gc01993f,10.3390/molecules24193523,10.1021/acscatal.9b00884,10.1021/acs.chemrev.8b00505,10.6023/cjoc201809037,10.1002/cjoc.201800237,10.1002/zaac.201800151,10.1021/acs.joc.8b01474#N/AJAN2018FALSEFALSEFALSEFALSE8186
70
30FALSEanie.20200239210.1002/anie.202002392https://sci-hub.wf/10.1002/anie.202002392https://doi.org/10.1002/anie.202002392NiC-O ActivationKellyTRUE243382020
Stradiotto, M
Nickel-Catalyzed Cross-Coupling of Sulfonamides With (Hetero)aryl Chlorides
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
The development of Ni-catalyzed C-N cross-couplings of sulfonamides with (hetero)aryl chlorides is reported. These transformations, which were previously achievable only with Pd catalysis, are enabled by use of air-stable (L)NiCl(o-tol) pre-catalysts (L=PhPAd-DalPhos and PAd2-DalPhos), without photocatalysis. The collective scope of (pseudo)halide electrophiles (X=Cl, Br, I, OTs, and OC(O)NEt2) demonstrated herein is unprecedented for any reported catalyst system for sulfonamide C-N cross-coupling (Pd, Cu, Ni, or other). Preliminary competition experiments and relevant coordination chemistry studies are also presented.
Dalhousie Univ6/2/2020Csp2_ar-Nsp3E-NuOH
OCONEt2
HHet
NHSO2R
No baseNo BaseMedium0.31_x10.1002/anie.202200352,10.1021/acscatal.1c03010,10.1002/anie.20201434010.1055/a-1735-6250,10.1002/anie.202200352,10.1021/acscatal.1c05386,10.1021/acscatal.1c05386,10.1016/j.jcat.2021.12.007,10.1016/j.jorganchem.2021.122145,10.1002/cctc.202101013,10.1039/d1ra06330h,10.1021/acscatal.1c03010,10.1002/cctc.202100803,10.1002/anie.202103803,10.1002/anie.202013976,10.1002/anie.202014340,10.1021/acs.orglett.0c03505,10.1021/acscatal.0c03857,10.1039/d0cc06787c,10.1055/s-0040-1705972,10.1021/acs.oprd.0c00367,10.1021/acs.orglett.0c02672,10.1002/chem.202002800,10.1021/acs.joc.0c001392/7/2022
71
76FALSEacs.orglett.9b0024210.1021/acs.orglett.9b00242https://sci-hub.wf/10.1021/acs.orglett.9b00242https://doi.org/10.1021/acs.orglett.9b00242NiC-N ActivationShihongTRUE311#N/A2019Xia, JB
Nickel-Catalyzed Kumada Coupling of Boc-Activated Aromatic Amines via Nondirected Selective Aryl C-N Bond CleavageORG LETT
A nickel-catalyzed Kumada coupling of aniline derivatives was developed by selective cleavage of aryl C-N bonds under mild reaction conditions. Without preinstallation of an ortho directing group on anilines, the cross-coupling reactions of Boc-protected aromatic amines with aryl Grignard reagents afforded unsymmetric biaryls. Mechanistic studies by DFT calculations revealed that the nickel-mediated C-N bond cleavage is the rate-limiting step.
Univ Chinese Acad Sci
2/15/2019Csp2_ar-Csp2_arE-NuNMg
N(Ph)Boc
MgXArylArylNo baseNo Base_10.1021/acscatal.1c05738,10.1021/acs.orglett.1c03590,10.1021/acs.orglett.1c01503,10.1039/d1gc00141h,10.1021/acs.joc.0c02992,10.1021/acs.orglett.0c03660,10.1055/s-0040-1705986,10.1002/chem.202003213,10.1021/acs.joc.0c02266,10.1021/acs.joc.0c01274,10.1021/acs.orglett.0c02105,10.1016/j.catcom.2020.106009,10.1021/acscatal.0c01000,10.1021/jacs.0c02405,10.1021/acs.joc.0c00227,10.1021/acs.orglett.0c00679,10.1021/acs.orglett.0c00736,10.1002/chem.202000412,10.1055/s-0039-1690703,10.1021/acs.joc.9b02826,10.1039/c9qo01177c,10.1016/j.tet.2019.130777,10.1039/c9sc03169c,10.1021/acs.orglett.9b02961,10.1021/acs.joc.9b02013,10.1021/acscatal.9b02440,10.1002/slct.201902137,10.1021/acs.joc.9b00962,10.1021/acs.orglett.9b01053Long12/22/2021
72
77FALSEacs.organomet.6b0020110.1021/acs.organomet.6b00201https://sci-hub.wf/10.1021/acs.organomet.6b00201https://doi.org/10.1021/acs.organomet.6b00201NiC-H ActivationGerryTRUE301#N/A2016Punji, B
Synthesis of Quinoline-Based NNN-Pincer Nickel(II) Complexes: A Robust and Improved Catalyst System for C-H Bond Alkylation of Azoles with Alkyl Halides
ORGANOMETALLICS
The quinoline-based pincer nickel(II) complexes kappa(N),kappa(N),kappa(N) -{R2N-C6H4-(mu-N)-C9H6N}NiX (((NNNQ)-N-R2)NiCl: R = Me) 2a; R = Et, 2b) were synthesized by the reaction of the ligand precursors ((NNNQ)-N-R2)H (R = Me, 1a; R = Et, 1b) with (DME)NiCl2 in the presence of Et3N. Similarly, the pincer mickel(II) derivatives ((NNNQ)-N-R2)NiX (R = Me, X = Br, 3a; R = Et, X = Br, 3b; R = Me, X = OAc, 4a) were obtained by treatment of the ligands ((NNNQ)-N-R2)H with the nickel precursor (THF)(2)NiBr2 or Ni(QAc)(2). All of these complexes were characterized by H-1 and C-13 NMR spectroscopy as well as by elemental analysis. Further, the molecular structures of 2a and 3a,b were elucidated by X-ray crystallography. Complex 2a is found to be an efficient catalyst for the direct C-H bond alkylation of substituted benzothiazoles and oxazoles with various unactivated alkyl halides containing beta-hydrogens under mild reaction conditions. The catalyst 2a is very robust and was recycled and reused five times for the alkylation reaction without a decrease in its catalytic activity. Preliminary studies reveal that the catalyst 2a acts as an active catalyst and the alkylation reaction appears to operate via a radical pathway.
CSIR NCL6/13/2016yCsp3-Csp2_arE-NuXHBrHAlkylHetLiOtBuIonic-OtBu_xxx10.1021/acscatal.6b0200310.1002/tcr.202100113,10.1039/d1nj01698a,10.1039/d0dt03593a,10.1021/acscatal.0c05580,10.1016/bs.adomc.2021.04.003,10.1021/acs.inorgchem.0c01401,10.1021/acssuschemeng.0c03415,10.1021/acs.joc.0c00530,10.1021/acs.organomet.0c00161,10.1016/j.chempr.2020.04.005,10.1016/j.ica.2019.119283,10.1002/adsc.201900586,10.1021/acs.organomet.9b00060,10.1002/anie.201806631,10.1021/acs.chemrev.8b00507,10.1039/c8dt03210f,10.1002/adsc.201800659,10.1002/slct.201801647,10.1021/acs.inorgchem.8b00958,10.1039/c8ob01108g,10.1002/ajoc.201800243,10.1021/acs.organomet.8b00025,10.1007/s11172-018-2086-7,10.1002/adsc.201700542,10.1021/acs.orglett.7b01946,10.1007/s12039-017-1338-7,10.1002/cssc.201700321,10.1002/chem.201605306,10.1021/acs.organomet.6b00810,10.1021/acscatal.6b0200312/28/2021
73
14FALSEanie.20200411610.1002/anie.202004116https://sci-hub.wf/10.1002/anie.202004116https://doi.org/10.1002/anie.202004116NiC-O ActivationKellyTRUE111562020Qing, FL
Nickel-Mediated Trifluoromethylation of Phenol Derivatives by Aryl C-O Bond Activation
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
The increasing pharmaceutical importance of trifluoromethylarenes has stimulated the development of more efficient trifluoromethylation reactions. Tremendous efforts have focused on copper- and palladium-mediated/catalyzed trifluoromethylation of aryl halides. In contrast, no general method exists for the conversion of widely available inert electrophiles, such as phenol derivatives, into the corresponding trifluoromethylated arenes. Reported herein is a practical nickel-mediated trifluoromethylation of phenol derivatives with readily available trimethyl(trifluoromethyl)silane (TMSCF3). The strategy relies on PMe3-promoted oxidative addition and transmetalation, and CCl3CN-induced reductive elimination. The broad utility of this transformation has been demonstrated through the direct incorporation of trifluoromethyl into aromatic and heteroaromatic systems, including biorelevant compounds.
Chinese Acad Sci9/7/2020TRUEFALSEFALSECsp2_ar-Csp3E-NuOSiOPivSiMe3ArylAlkylNo baseNo BaseMedium0.33_x10.1039/d2dt00511e,10.1039/d2ob00056c,10.1002/anie.202115592,10.1002/ejoc.202100937,10.1039/d1ob01410b,10.1039/d1cy01254a,10.1039/d1cc04038c,10.1016/j.jfluchem.2020.109695,10.6023/cjoc202000074 Long 11/10/2021SEP 72020FALSEFALSEFALSEFALSE593716076
74
79FALSEejoc.20140323410.1002/ejoc.201403234https://sci-hub.wf/10.1002/ejoc.201403234https://doi.org/10.1002/ejoc.201403234NiC-H ActivationGerryTRUE301#N/A2014Zhang, Y
Nickel-Catalyzed Decarboxylative Arylation of Heteroarenes through sp(2) C-H Functionalization
EUR J ORG CHEM
The direct decarboxylative arylation of hetereoarenes with benzoic acids through a nickel-catalyzed sp(2) C-H functionalization process was developed. This process provides the first examples of decarboxylative cross-coupling reactions with aromatic acids through nickel catalysis and tolerates a variety of functional groups. Moreover, this method provides efficient access to 2-aryl-substituted azoles, an important structural unit in natural products, medicinal compounds, and functional materials.
Nanjing Univ10/21/2014Csp2_ar-Csp2_arE-NuCsp2HCOOHHArylHetAg2CO3#N/A#N/A_x10.1021/acs.orglett.5b0024110.1002/jhet.4311,10.1002/tcr.202100113,10.1039/d1cs00216c,10.1016/j.chempr.2020.04.005,10.1039/c9qo01073d,10.1002/ejoc.201901309,10.1007/s10593-019-02475-9,10.1055/s-0037-1609636,10.1021/acs.chemrev.8b00507,10.1021/jacs.7b13305,10.1039/c7gc02949g,10.1109/TrustCom/BigDataSE.2018.00142,10.1002/ejoc.201701187,10.1021/acs.joc.7b01686,10.1021/acs.orglett.7b02730,10.1021/jacs.7b05155,10.1021/acscatal.7b01330,10.1021/acs.chemrev.6b00516,10.1002/ejoc.201700121,10.1021/acscatal.7b01683,10.1021/acs.joc.6b02211,10.1021/acs.orglett.6b01632,10.1007/s41061-016-0053-z,10.1021/acs.joc.6b00883,10.1039/c6cc04486g,10.1021/acs.joc.5b01450,10.1016/j.jorganchem.2015.03.023,10.1021/acs.orglett.5b00241,10.1039/c5qo00040h12/29/2021
75
15FALSEanie.20200682610.1002/anie.202006826https://sci-hub.wf/10.1002/anie.202006826https://doi.org/10.1002/anie.202006826NiC-O ActivationShihongTRUE10162020Amgoune, A
Nickel-Catalyzed Mono-Selective alpha-Arylation of Acetone with Aryl Chlorides and Phenol Derivatives
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
The challenging nickel-catalyzed mono-alpha-arylation of acetone with aryl chlorides, pivalates, and carbamates has been achieved for the first time. A nickel/Josiphos-based catalytic system is shown to feature unique catalytic behavior, allowing the highly selective formation of the desired mono-alpha-arylated acetone. The developed methodology was applied to a variety of (hetero)aryl chlorides including biologically relevant derivatives. The methodology has been extended to the unprecedented coupling of acetone with phenol derivatives. Mechanistic studies allowed the isolation and characterization of key Ni(0)and Ni(II)catalytic intermediates. The Josiphos ligand is shown to play a key role in the stabilization of Ni(II)intermediates to allow a Ni-0/Ni(II)catalytic pathway. Mechanistic understanding was then leveraged to improve the protocol using an air-stable Ni(II)pre-catalyst.
Univ Lyon 110/19/2020Csp2_ar-Csp2E-NuOHOPivHAryl
Carbonyl
Cs2CO3Ionic-CO3Medium0.33_x10.1039/d1qo01765a,10.1021/acs.orglett.2c00334,10.1039/d1sc05451a,10.2533/chimia.2021.943,10.1021/acssuschemeng.1c05237,10.1021/acs.organomet.1c00369,10.3762/bjoc.17.126,10.1021/acs.oprd.1c00053,10.2174/15701794186662102241249311/6/2022
76
22FALSEanie.20201103610.1002/anie.202011036https://sci-hub.wf/10.1002/anie.202011036https://doi.org/10.1002/anie.202011036NiC-O ActivationKellyTRUE18272021Zhou, JS
Enantioselective Intermolecular Heck and Reductive Heck Reactions of Aryl Triflates, Mesylates, and Tosylates Catalyzed by Nickel
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Nickel-catalyzed intermolecular Heck reaction of cycloalkenes proceeds well with aryl triflates, mesylates and tosylates in excellent enantiomeric ratios. The asymmetric reductive Heck reaction also works with a 2-cyclopentenone ketal, which is equivalent to conjugate arylation of the enone itself.
Nanyang Technol Univ
2/8/2021TRUEFALSEFALSECsp2_ar-Csp3E-NuOHOTfHArylAlkylNo baseNo BaseWeak0.53_x10.1039/d1cc00634g,10.1002/anie.20211455610.1002/ejoc.202101384,10.1039/d1ob02360h,10.1002/anie.202114556,10.1021/jacs.1c09214,10.1038/s41467-021-26194-y,10.1039/d1ob01806j,10.6023/cjoc202105016,10.6023/cjoc202103015,10.1021/acs.oprd.1c00241,10.1055/a-1523-3228,10.1039/d1cc00634g11/10/2021FEB 82021FALSEFALSEFALSEFALSE6062828
77
3FALSEanie.20201434010.1002/anie.202014340https://sci-hub.wf/10.1002/anie.202014340https://doi.org/10.1002/anie.202014340NiC-O ActivationGerryTRUE72382021
Stradiotto, M
Nickel-Catalyzed N-Arylation of Fluoroalkylamines
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
The Ni-catalyzed N-arylation of beta-fluoroalkylamines with broad scope is reported for the first time. Use of the air-stable pre-catalyst (PAd2-DalPhos)Ni(o-tol)Cl allows for reactions to be conducted at room temperature (25 degrees C, NaOtBu), or by use of a commercially available dual-base system (100 degrees C, DBU/NaOTf), to circumvent decomposition of the N-(beta-fluoroalkyl)aniline product. The mild protocols disclosed herein feature broad (hetero)aryl (pseudo)halide scope (X=Cl, Br, I, and for the first time phenol-derived electrophiles), encompassing base-sensitive substrates and enantioretentive transformations, in a manner that is unmatched by any previously reported catalyst system.
Dalhousie Univ2/19/2021TRUEFALSEFALSECsp2_ar-Nsp3E-NuOHOTfHAryl
N(H)Alkyl
NitrogenNitrogen(neutral)Weak0.53_x10.1021/acscatal.1c03010,10.1002/anie.20220035210.1002/anie.202200352,10.1021/acscatal.1c05386,10.1021/acscatal.1c05386,10.1039/d1cc06688a,10.1039/d1ra06330h,10.1021/acscatal.1c03010,10.1055/a-1337-6459checked by Kelly2/22/2022FEB 192021FALSEFALSEFALSEFALSE6084080
78
13FALSEanie.20210332710.1002/anie.202103327https://sci-hub.wf/10.1002/anie.202103327https://doi.org/10.1002/anie.202103327NiC-O ActivationShihongTRUE51152021Newman, SG
Direct Synthesis of Ketones from Methyl Esters by Nickel-Catalyzed Suzuki-Miyaura Coupling
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
The direct conversion of alkyl esters to ketones has been hindered by the sluggish reactivity of the starting materials and the susceptibility of the product towards subsequent nucleophilic attack. We have now achieved a cross-coupling approach to this transformation using nickel, a bulky N-heterocyclic carbene ligand, and alkyl organoboron coupling partners. 65 alkyl ketones bearing diverse functional groups and heterocyclic scaffolds have been synthesized with this method. Catalyst-controlled chemoselectivity is observed for C(acyl)-O bond activation of multi-functional substrates bearing other bonds prone to cleavage by Ni, including aryl ether, aryl fluoride, and N-Ph amide functional groups. Density functional theory calculations provide mechanistic support for a Ni-0/Ni-II catalytic cycle and demonstrate how stabilizing non-covalent interactions between the bulky catalyst and substrate are critical for the reaction's success.
Univ Ottawa6/7/2021TRUETRUEFALSECsp2-Csp3E-NuOBOMe9-BBN
Carbonyl
AlkylK3PO4Ionic-PO4Strong-0.28_xxx10.1021/acs.oprd.1c00410,10.1021/acs.oprd.1c00410,10.1002/anie.202114731,10.1021/acscatal.1c03980 Long 11/5/2021JUN 72021FALSEFALSEFALSEFALSE602413476
79
9FALSEanie.20211039110.1002/anie.202110391https://sci-hub.wf/10.1002/anie.202110391https://doi.org/10.1002/anie.202110391NiC-O ActivationGerryTRUE3122022Li, C
Chemoselective and Diastereoselective Synthesis of C-Aryl Nucleoside Analogues by Nickel-Catalyzed Cross-Coupling of Furanosyl Acetates with Aryl Iodides
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Canonical nucleosides are vulnerable to enzymatic and chemical degradation, yet their stable mimics-C-aryl nucleosides-have demonstrated potential utility in medicinal chemistry, chemical biology, and synthetic biology, although current synthetic methods remain limited in terms of scope and selectivity. Herein, we report a cross-electrophile coupling to prepare C-aryl nucleoside analogues from readily available furanosyl acetates and aryl iodides. This nickel-catalyzed modular approach is characterized by mild reaction conditions, broad substrate scope, excellent beta-selectivity, and high functional-group compatibility. The exclusive chemoselectivity with respect to the aryl iodide enables efficient preparation of a variety of C-aryl halide furanosides suitable for various downstream transformations. The practicality of this transformation is demonstrated through the synthesis of a potent analogue of a naturally occurring NF-kappa B activator.
Tsinghua Univ1/3/2022Csp3-Csp2_arE-EOXOAcIAlkylArylNo baseNo BaseMedium0.31_10.1080/07328303.2022.20312072/16/2022
80
8FALSEanie.20211455610.1002/anie.202114556https://sci-hub.wf/10.1002/anie.202114556https://doi.org/10.1002/anie.202114556NiC-O ActivationShihongTRUE8102022Shu, XZ
Reductive Alkylation of Alkenyl Acetates with Alkyl Bromides by Nickel Catalysis
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Catalytic alkylation of stable alkenyl C-O electrophiles is synthetically appealing, but studies to date have typically focused on the reactions with alkyl Grignard reagents. We report herein a cross-electrophile reaction of alkenyl acetates with alkyl bromides. This work has enabled a new method for the synthesis of aliphatic alkenes from alkenyl acetates to be established that can be used to add more structural complexity and molecular diversity with enhanced functionality tolerance. The method allows for a gram-scale reaction and modification of biologically active molecules, and it affords access to useful building blocks. Preliminary mechanistic studies reveal that the Ni-I species plays an essential role for the success of the coupling of these two reactivity-mismatched electrophiles.
Lanzhou Univ1/21/2022Csp2-Csp3E-EOXOAcBrVinylAlkylNo baseNo BaseMedium0.31_10.1002/anie.2022000031/6/2022
81
303FALSEanie.20211473110.1002/anie.202114731https://sci-hub.wf/10.1002/anie.202114731https://doi.org/10.1002/anie.202114731NiC-O ActivationxWilliam12-JunTRUE71#N/A2022Yuan, WM
From Esters to Ketones via a Photoredox-Assisted Reductive Acyl Cross-Coupling Strategy
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
A method was developed for ketone synthesis via a photoredox-assisted reductive acyl cross-coupling (PARAC) using a nickel/photoredox dual-catalyzed cross-electrophile coupling of two different carboxylic acid esters. A variety of aryl, 1 degrees, 2 degrees, 3 degrees-alkyl 2-pyridyl esters can act as acyl electrophiles while N-(acyloxy)phthalimides (NHPI esters) act as 1 degrees, 2 degrees, 3 degrees-radical precursors. Our PARAC strategy provides an alternative and reliable way to synthesize various sterically congested 3 degrees-3 degrees, 3 degrees-2 degrees, and aryl-3 degrees ketones under mild and highly unified conditions, which have been otherwise difficult to access. The combined experimental and computational studies identified a Ni-0/Ni-I/Ni-III pathway for ketone formation.
1/17/2022Csp2-Csp3E-EOCsp2OPyCONHPI
Carbonyl
AlkylNo baseNo BaseStrong-0.326/21/2022
82
315FALSEanie.20211498110.1002/anie.202114981https://sci-hub.wf/10.1002/anie.202114981https://doi.org/10.1002/anie.202114981NiC-O ActivationxLong6-JulyTRUE111#N/A2022Cozzi, PG
Nickel-Mediated Enantioselective Photoredox Allylation of Aldehydes with Visible Light
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Here we report a practical, highly enantioselective photoredox allylation of aldehydes mediated by chiral nickel complexes with commercially available allyl acetate as the allylating agent. The methodology allows the clean stereoselective allylation of aldehydes in good to excellent yields and up to 93 % e.e. using a catalytic amount of NiCl2(glyme) in the presence of the chiral aminoindanol-derived bis(oxazoline) as the chiral ligand. The photoredox system is constituted by the organic dye 3DPAFIPN and a Hantzsch's ester as the sacrificial reductant. The reaction proceeds under visible-light irradiation (blue LEDs, 456 nm) at 8-12 degrees C. Compared to other published procedures, no metal reductants (such as Zn or Mn), additives (e.g. CuI) or air-sensitive Ni(COD)(2) are necessary for this reaction. Accurate DFT calculations and photophysical experiments have clarified the mechanistic picture of this stereoselective allylation reaction.
Csp3-Csp2E-NuOHOAcHAllyl
Carbonyl
No baseNo BaseMedium0.317/6/2022
83
258FALSEanie.20220035210.1002/anie.202200352https://sci-hub.wf/10.1002/anie.202200352https://doi.org/10.1002/anie.202200352NiC-O ActivationGerry2-MarTRUE11382022
Stradiotto, M
Mapping Dual-Base-Enabled Nickel-Catalyzed Aryl Amidations: Application in the Synthesis of 4-Quinolones
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
The C-N cross-coupling of (hetero)aryl (pseudo)halides with NH substrates employing nickel catalysts and organic amine bases represents an emergent strategy for the sustainable synthesis of (hetero)anilines. However, unlike protocols that rely on photoredox/electrochemical/reductant methods within Ni-I/III cycles, the reaction steps that comprise a putative Ni-0/II C-N cross-coupling cycle for a thermally promoted catalyst system using organic amine base have not been elucidated. Here we disclose an efficient new nickel-catalyzed protocol for the C-N cross-coupling of amides and 2 '-(pseudo)halide-substituted acetophenones, for the first time where the (pseudo)halide is chloride or sulfonate, which makes use of the commercial bisphosphine ligand PAd2-DalPhos (L4) in combination with an organic amine base/halide scavenger, leading to 4-quinolones. Room-temperature stoichiometric experiments involving isolated Ni-0,Ni- I,Ni- and II species support a Ni-0/II pathway, where the combined action of DBU/NaTFA allows for room-temperature amide cross-couplings.
3/21/2022Csp2_ar-Nsp3E-NuOHOTsHAryl
N(Alkyl)Carbonyl
NitrogenNitrogen(neutral)Weak0.36_10.1039/d1cy00374g,10.1002/anie.202016310,10.1002/chem.202003580,10.1002/anie.202014340,10.1055/a-1337-6459,10.1021/jacs.0c05901,10.1038/s41929-020-0473-6,10.1021/acs.joc.0c00139,10.1021/acscatal.0c00393,10.1021/jacs.9b13531,10.1002/anie.201916398,10.1002/anie.202002392,10.1021/jacs.0c00286,10.1038/s41929-019-0392-6,10.1021/jacs.9b11049,10.1016/j.trechm.2019.08.004,10.1021/acscatal.9b03715,10.1002/anie.201904795,10.1021/acs.orglett.9b02621,10.1021/acs.oprd.9b00196,10.1021/jacs.9b05461,10.1016/j.chempr.2019.01.006,10.1002/anie.201900095,10.1021/acscatal.9b00981,10.1021/acs.orglett.9b00698,10.1021/jacs.9b01886,10.1002/chem.201805987,10.1002/anie.201812862,10.1021/acscatal.8b01879,10.3389/fcimb.2018.00230,10.1021/acscatal.8b00856,10.1002/anie.201800699,10.1055/s-0036-1590819,10.1002/ejoc.201700660,10.1021/jacs.7b01463,10.1021/acscatal.6b02988,10.1002/anie.201604429,10.1038/ncomms11073,10.1021/acscatal.5b02021,10.1002/anie.201500404,10.1002/anie.201410875,10.1021/ja411911s,10.1021/ol403209k,10.1039/c3cs60289c,10.1021/ja3116718,10.1055/s-0031-1291146,10.1246/cl.2011.375,10.1021/ja900805y,10.1021/ol800837z,10.1021/jo701384n3/9/2022
84
89FALSEs-0036-158884510.1055/s-0036-1588845https://sci-hub.wf/10.1055/s-0036-1588845https://doi.org/10.1055/s-0036-1588845NiC-N ActivationKellyTRUE343#N/A2017Szostak, M
Nickel-Catalyzed Negishi Cross-Coupling of N-Acylsuccinimides: Stable, Amide-Based, Twist-Controlled Acyl-Transfer Reagents via N-C Activation
SYNTHESIS-STUTTGART
This paper reports a room temperature, nickel-catalyzed Negishi cross-coupling of N-acylsuccinimides with arylzinc reagents via selective N-C bond cleavage enabled by amide bond twist. The reaction proceeds using a commercially available, air-stable Ni(II) precatalyst in the absence of additives under exceedingly mild conditions. Of broad interest, this report introduces N-acylsuccinimides as stable, crystalline, electrophilic, cost-effective, benign, amide-based acyl transfer reagents via acyl metal intermediates. The reaction selectivity is governed by half-twist of the amide bond in N-acylsuccinimides, thus opening the door for applications in metal-catalyzed manifolds via redox-neutral reaction pathways tuneable by amide bond distortion.
Rutgers State Univ8/1/2017Csp2-Csp2_arE-NuNZn
pyrrolidine-2,5-dione
ZnX
Carbonyl
ArylNo baseNo Base_10.1021/acs.orglett.9b04497,10.1021/acscatal.7b03688,10.1021/jacs.7b1286510.1021/acs.orglett.1c03473,10.1039/d1qo00992c,10.1002/asia.202100691,10.1002/cctc.202100672,10.1021/acs.orglett.0c03260,10.1021/acscatal.0c03334,10.1055/s-0040-1707301,10.1055/s-0040-1707101,10.1021/acsomega.0c02309,10.1021/acs.oprd.0c00054,10.1021/acs.orglett.0c00885,10.1021/acs.orglett.0c00442,10.1002/ejoc.201901730,10.1021/acs.orglett.9b04497,10.1021/acs.orglett.9b03434,10.1002/adsc.201900819,10.1002/adsc.201900485,10.1080/00397911.2019.1594306,10.1016/j.tet.2019.03.047,10.1002/adsc.201801577,10.1021/acs.jchemed.8b00489,10.3390/catal9020129,10.1002/asia.201801317,10.3390/catal9010053,10.1016/j.jorganchem.2018.09.026,10.1039/c8cs00335a,10.1039/c8qo00591e,10.3390/molecules23102681,10.1021/acs.oprd.8b00182,10.1002/ejoc.201800109,10.1021/jacs.7b12865,10.1021/acscatal.7b03688,10.1021/jacs.7b09482Long2/17/2022
85
124FALSEchem.20090278510.1002/chem.200902785https://sci-hub.wf/10.1002/chem.200902785https://doi.org/10.1002/chem.200902785NiC-O ActivationShihongTRUE6312282010Shi, ZJ
Construction of Polysubstituted Olefins through Ni-Catalyzed Direct Activation of Alkenyl C-O of Substituted Alkenyl Acetates
CHEMISTRY-A EUROPEAN JOURNAL
Peking Univ5/14/2010Csp2-Csp2_arE-NuOBOAcB(OH)2VinylArylK3PO4Ionic-PO4Medium0.31_10.1038/s41467-020-20725-9,10.1002/chem.201103050,10.1246/cl.2011.913,10.1021/ol4011757,10.1002/anie.202114556,10.1021/jacs.9b05224,10.1021/ol203322v,10.1021/acscatal.6b00801,10.1021/jacs.8b02134,10.1002/chem.201003731,10.1021/jo1024464,10.1016/j.tet.2012.04.00510.1002/anie.202114556,10.1039/d1ob00955a,10.1002/anie.202103465,10.1038/s41467-020-20725-9,10.1055/a-1306-3228,10.1002/anie.202006586,10.1021/acs.orglett.0c01127,10.1021/jacs.9b08586,10.1021/jacs.9b05224,10.1016/j.tetlet.2019.04.042,10.1055/s-0037-1611720,10.1021/acs.orglett.8b02824,10.1002/adsc.201800729,10.1002/anie.201805486,10.1021/jacs.8b02134,10.1016/j.tet.2017.09.052,10.1002/ajoc.201700342,10.1002/adsc.201700654,10.1021/acscatal.7b00245,10.1038/s41570-017-0025,10.1246/cl.160712,10.1002/anie.201605744,10.1007/s41061-016-0043-1,10.1021/acscatal.6b00801,10.1016/bs.adomc.2016.07.001,10.1039/c6cc07032a,10.1039/c5ra27859g,10.1002/anie.201504524,10.1021/ar500345f,10.1021/ja512498u,10.1021/jo501615a,10.1016/j.tet.2014.06.037,10.1021/ol5017367,10.1021/jo500561z,10.1515/pac-2014-5038,10.1002/asia.201300688,10.1016/j.tet.2013.05.030,10.1021/ol4011757,10.1007/3418_2012_42,10.1039/c3cs35521g,10.1002/adsc.201200364,10.1002/ejoc.201200368,10.1016/j.tet.2012.04.005,10.1002/chem.201200039,10.1021/ol203322v,10.1002/ejoc.201101284,10.1002/chem.201103050,10.1021/ja207759e,10.1021/ja2059999,10.1246/cl.2011.913,10.1246/cl.2011.1001,10.1246/cl.2011.907,10.1021/ol201620g,10.1002/chem.201003731,10.1021/jo1024464,10.1021/cr100259t,10.1002/chem.201002273,10.1021/ar100082dKelly11/25/2021
86
106FALSEchem.20100042010.1002/chem.201000420https://sci-hub.wf/10.1002/chem.201000420https://doi.org/10.1002/chem.201000420NiC-O ActivationKellyTRUE5411322010Han, FS
Aryl Phosphoramides: Useful Electrophiles for Suzuki-Miyaura Coupling Catalyzed by a NiCl2/dppp System (dppp=1,3-Bis(diphenylphosphino)propane)
CHEMISTRY-A EUROPEAN JOURNAL
Chinese Acad Sci4/23/2010Csp2_ar-Csp2_arE-NuOBOBOPB(OH)2ArylArylNo baseNo BaseStrong0.04_10.1021/jacs.6b11412,10.1002/anie.201101461,10.1021/ol201437g,10.1021/jo1024464,10.1021/jo2000034,10.1021/jo4005537,10.1002/adsc.201000710,10.1002/chem.201003403,10.1002/ejoc.201200444,10.1002/adsc.201400460,10.1039/c0cc03107k10.1021/acsinfecdis.1c00611,10.1021/acs.inorgchem.1c01720,10.1055/a-1349-3543,10.1021/acs.chemrev.9b00682,10.1021/acs.orglett.0c01123,10.1002/cjoc.201900506,10.1039/c9ob00313d,10.1016/j.tet.2018.10.025,10.3390/molecules23071715,10.1055/s-0036-1588508,10.1016/j.tet.2017.04.034,10.1021/acscatal.6b02912,10.1021/jacs.6b11412,10.1021/acscatal.6b02964,10.1016/j.jorganchem.2016.09.026,10.1055/s-0035-1562343,10.1016/j.tetlet.2015.10.009,10.1021/acs.orglett.5b01466,10.1016/j.tet.2015.04.052,10.1016/j.jorganchem.2015.01.009,10.1021/ol503560e,10.1039/c5ra12742d,10.1002/aoc.3227,10.1002/adsc.201400460,10.1002/ejoc.201402919,10.1007/s11426-014-5138-3,10.1021/cs4009946,10.6023/cjoc201307035,10.1002/aoc.3000,10.1021/jo4005537,10.1002/cctc.201200417,10.1039/c3cs35521g,10.1002/adsc.201200364,10.1002/chem.201103723,10.1002/ejoc.201200444,10.1002/ejoc.201200368,10.1039/c2cc31718d,10.1021/ja207759e,10.1246/cl.2011.907,10.1021/ol201437g,10.1002/adsc.201100101,10.1021/jo2000034,10.1021/jo1024464,10.1002/chem.201003403,10.1021/cr100259t,10.1002/adsc.201000710,10.1002/anie.201101461,10.1039/c1cs15100b,10.1002/chem.201002273,10.1039/c0cc03107kKelly1/11/2022
87
92FALSEs41467-019-12949-110.1038/s41467-019-12949-1https://sci-hub.wf/10.1038/s41467-019-12949-1https://doi.org/10.1038/s41467-019-12949-1NiC-H ActivationShihongTRUE411#N/A2019
Xue, XS; Zhao, DB
Nickel-catalyzed intermolecular oxidative Heck arylation driven by transfer hydrogenationNAT COMMUN
The conventional oxidative Heck reaction between aryl boronic acids and alkenes typically involved the Pd-II/Pd-0/Pd-II catalytic cycle incorporating an external oxidant and often suffered C=C bond isomerization for internal alkyl-substituted alkenes via chain-walking. Herein, we demonstrate that the regioselectivity (gamma-selectivity vs. delta-selectivity) and pathway selectivity (hydroarylation vs. oxidative Heck coupling) of a directed Ni-catalyzed alkene arylation can be controlled by judicious tuning of the coordination environment around the nickel catalyst via optimization of an appropriate phosphine ligand and directing group. In this way, the Ni (0)-catalyzed oxidative Heck arylation that relies on transfer hydrogenation of an acceptor olefin is developed with excellent E/Z selectivity and regioselectivity. Mechanistic investigations suggest that the addition of the acceptor is crucial for lowering the energy for carbometalation and for enabling catalytic turnover.
Nankai Univ11/5/2019Csp2_ar-Csp2Nu-NuBHB(OH)2HArylVinylCsOPivIonic-ORNu-M_10.1039/d1qo01579f,10.1039/d1cc05125c,10.1016/j.xcrp.2021.100574,10.1038/s41467-021-26194-y,10.1038/s41467-021-25696-z,10.1016/j.tet.2021.132435,10.1021/jacs.1c05834,10.1016/j.tet.2021.132279,10.1039/d1sc03121j,10.1002/anie.202105355,10.1021/acscatal.1c00908,10.1021/acscatal.1c00625,10.1016/j.rser.2021.111103,10.1021/acs.orglett.1c01007,10.1021/jacs.1c01138,10.1021/jacs.0c12333,10.1016/j.jcat.2020.11.019,10.1002/anie.202012614,10.1021/acs.orglett.0c03542,10.1021/jacs.0c10333,10.6023/cjoc202000075,10.1002/cctc.202001425,10.1002/anie.202010840,10.1002/cjoc.202000376,10.1002/anie.202009195,10.1021/acs.orglett.0c02053,10.1021/acs.orglett.0c01607,10.1002/anie.202003830,10.1021/jacs.0c03040,10.1021/acs.orglett.0c01365,10.1021/acs.orglett.0c00963,10.1002/anie.2020017421/5/2022
88
100FALSEchem.20100340310.1002/chem.201003403https://sci-hub.wf/10.1002/chem.201003403https://doi.org/10.1002/chem.201003403NiC-O ActivationLongTRUE527322011Han, FS
Nickel-Catalyzed Cross-Coupling of Phenols and Arylboronic Acids Through an In Situ Phenol Activation Mediated by PyBroP
CHEMISTRY-A EUROPEAN JOURNAL
A new method for the Suzuki-Miyaura cross-coupling of phenols and arylboronic acids through in situ phenol activation mediated by PyBroP is presented. The reaction proceeds efficiently by using cost-effective, markedly stable [NiCl2(dppp)] (dppp = 1,3-bis(diphenylphosphino) propane) as the catalyst in only 5 mol% loading, as well as in the absence of extra ligands. The method exhibits broad applicability and high efficiency towards a wide range of both phenols and boronic acids, including activated, nonactivated, deactivated, and heteroaromatic coupling partners. In addition, various functional groups, such as ether, amino, cyano, ester, and ketone groups, are compatible with this transformation. Notably, arylboronic acids containing an unprotected NH2 group and 2-heterocyclic boronic acids, which are generally problematic for coupling under conventional conditions, are also viable substrates, although moderate yields were obtained for sterically hindered substrates. Consequently, the in situ cross-coupling methodology coupled with the use of an inexpensive and stable nickel catalyst provides a rapid and efficient pathway for the assembly of biaryls and heterobiaryls with structural diversity from readily available phenol compounds.
Chinese Acad Sci3/1/2011Csp2_ar-Csp2_arE-NuOBOHB(OH)2ArylArylIonic-PO4Strong-0.81_10.1002/anie.201101461,10.1002/chem.201103784,10.1021/ol201437g,10.1002/ejoc.201200444,10.1002/adsc.201400460,10.1021/jacs.6b11412,10.1021/jo400553710.1039/d1ra08771a,10.1016/j.tet.2021.132431,10.1055/a-1349-3543,10.1021/acscatal.0c03334,10.1021/acs.chemrev.0c00088,10.1002/cjoc.201900506,10.1055/s-0039-1690740,10.1002/aoc.5383,10.1039/c8qo00729b,10.3390/molecules23112740,10.1002/aoc.4273,10.1002/ajoc.201700450,10.1038/s41570-017-0025,10.1021/jacs.6b11412,10.1021/acs.joc.6b02093,10.1016/j.jorganchem.2016.09.026,10.1007/s41061-016-0043-1,10.1002/ejoc.201600356,10.3390/molecules20057528,10.1016/j.jorganchem.2015.01.009,10.1021/ol503560e,10.1039/c5ra12742d,10.1248/yakushi.14-00192,10.1002/adsc.201400460,10.1002/ejoc.201402919,10.1002/ejoc.201402475,10.1007/s11426-014-5138-3,10.1007/s11434-014-0239-0,10.1021/jo500619f,10.1021/om5001327,10.1021/cs4009946,10.6023/cjoc201307035,10.1039/c3dt52412d,10.1039/c4ob01041h,10.1002/asia.201300688,10.1021/jo4005537,10.1016/j.tet.2012.10.080,10.1039/c3cs35521g,10.1055/s-0032-1317076,10.1002/chem.201103723,10.1002/ejoc.201200444,10.1002/ejoc.201200368,10.1002/chem.201103784,10.1039/c2cc31718d,10.1002/aoc.1822,10.1021/ol201437g,10.1002/adsc.201100101,10.1002/anie.201101461,10.1039/c1cc15753aKelly2/10/2022
89
94FALSEanie.20200227110.1002/anie.202002271https://sci-hub.wf/10.1002/anie.202002271https://doi.org/10.1002/anie.202002271NiC-N ActivationLongTRUE472382020Weix, DJ
Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids
ANGEW CHEM INT EDIT
While ketones are among the most versatile functional groups, their synthesis remains reliant upon reactive and low-abundance starting materials. In contrast, amide formation is the most-used bond-construction method in medicinal chemistry because the chemistry is reliable and draws upon large and diverse substrate pools. A new method for the synthesis of ketones is presented here that draws from the same substrates used for amide bond synthesis: amines and carboxylic acids. A nickel terpyridine catalyst couples N-alkyl pyridinium salts with in situ formed carboxylic acid fluorides or 2-pyridyl esters under reducing conditions (Mn metal). The reaction has a broad scope, as demonstrated by the synthesis of 35 different ketones bearing a wide variety of functional groups with an average yield of 60 +/- 16 %. This approach is capable of coupling diverse substrates, including pharmaceutical intermediates, to rapidly form complex ketones.
Univ Wisconsin8/3/2020TRUETRUETRUECsp3-Csp2E-ENO
Triphenylpyridinium+BF4-
OPyAlkyl
Carbonyl
No baseNo Base_xx10.1002/anie.202103327,10.1038/s41467-021-25222-110.1002/adsc.202200003,10.1055/s-0040-1719881,10.1039/d1cs01084k,10.1002/ejoc.202101440,10.1021/jacs.1c10932,10.1021/acscatal.1c04235,10.1002/anie.202114731,10.1021/jacs.1c10150,10.1002/anie.202112454,10.1039/d1qo01438b,10.1039/d1qo01219c,10.1021/acscatal.1c02307,10.1021/acs.orglett.1c02708,10.1055/a-1649-5460,10.1021/acs.orglett.1c02458,10.1021/jacs.1c07780,10.1038/s41467-021-25222-1,10.1039/d1nj02677a,10.1246/bcsj.20210148,10.1021/acscatal.1c01860,10.1021/acs.orglett.1c01716,10.1039/d1sc01217g,10.1016/j.tetlet.2021.153071,10.1002/anie.202103327,10.1002/cjoc.202000662,10.1002/tcr.202100053,10.1039/d1sc00986a,10.1021/jacs.1c02629,10.1002/anie.202015835,10.1002/ejoc.202001193,10.1002/anie.202014660,10.1016/j.tetlet.2020.152624,10.1021/acs.orglett.0c03342,10.1021/jacs.0c10471,10.1021/acscatal.0c03237,10.1021/acscatal.0c03903,10.1021/jacs.0c08595,10.1039/d0sc03833d,10.1021/acs.orglett.0c01592Long11/12/2021AUG 32020FALSEFALSEFALSEFALSE593213484
90
164FALSEchem.20100373110.1002/chem.201003731https://sci-hub.wf/10.1002/chem.201003731https://doi.org/10.1002/chem.201003731NiC-O ActivationShihongTRUE851952011Wang, ZX
Cross-Coupling of Aryl/Alkenyl Ethers with Aryl Grignard Reagents through Nickel-Catalyzed C-O Activation
CHEMISTRY-A EUROPEAN JOURNAL
Univ Sci & Technol China
4/1/2011Csp2_ar-Csp2_arE-NuOMgOMeMgXArylArylNo baseNo BaseStrong-0.28_10.1002/anie.201806790,10.1039/c4cc08187k,10.1021/jacs.7b04973,10.1021/ol502583h,10.1002/chem.201603436,10.1002/chem.201103784,10.1021/ol302112q,10.1246/cl.150936,10.1002/anie.201402922,10.1021/acs.orglett.5b02200,10.1021/acscatal.7b01058,10.1021/ol503707m,10.1021/acs.orglett.6b02656,10.1021/ol4011757,10.1021/acs.organomet.5b00874,10.1002/anie.201101461,10.1021/jacs.8b02134,10.1002/ejic.201900692,10.1021/ja307045r10.1002/ejoc.202100955,10.1039/d1ob01503f,10.1039/c9cs00571d,10.1021/acscatal.1c01077,10.1055/a-1349-3543,10.1055/s-0040-1705986,10.1021/acs.chemrev.0c00088,10.1021/acs.orglett.0c02236,10.1021/acs.orglett.9b02504,10.1021/acs.joc.9b01879,10.1002/cjoc.201800554,10.1002/ejic.201900692,10.1002/cjoc.201800575,10.1055/s-0037-1611663,10.1021/acs.organomet.8b00720,10.1007/3418_2018_19,10.1002/chem.201803297,10.1002/anie.201806790,10.1016/j.jorganchem.2018.01.019,10.1038/s41467-018-03928-z,10.1021/acs.orglett.8b00313,10.1021/jacs.8b02134,10.1039/c7cc08709h,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.1002/chem.201703266,10.1021/acs.joc.7b01711,10.1021/jacs.7b04973,10.1021/acscatal.7b02025,10.1248/cpb.c17-00487,10.1021/acscatal.7b01058,10.1039/c6nj03876j,10.1021/acs.joc.6b02354,10.1002/ejoc.201601098,10.1021/acs.orglett.6b02656,10.1246/cl.160712,10.1002/chem.201603436,10.1021/acs.joc.6b01648,10.1002/asia.201600972,10.1002/chem.201602150,10.1007/s41061-016-0043-1,10.1002/ejoc.201501570,10.1016/bs.adomc.2016.07.001,10.1021/acs.organomet.5b00874,10.1246/cl.150936,10.1021/jacs.5b08621,10.1021/acs.joc.5b01787,10.1002/anie.201505789,10.1002/chem.201502114,10.1021/acs.orglett.5b02200,10.1246/cl.150359,10.1021/acs.orglett.5b01229,10.1021/acs.accounts.5b00051,10.1021/ol503707m,10.1039/c5qo00001g,10.1039/c4cc08187k,10.1002/anie.201402922,10.1021/ol502583h,10.1002/chem.201404380,10.1021/ja5043534,10.1002/adsc.201301081,10.1002/anie.201304268,10.1039/c4ob00604f,10.3184/174751914X13857348538466,10.1039/c4cs00206g,10.1002/cctc.201300177,10.1021/ol4011757,10.1016/j.tetlet.2013.01.008,10.1021/ja311940s,10.1002/ajoc.201200185,10.1039/c3ra44884c,10.1021/ol3029059,10.1021/ja307045r,10.1021/ol302112q,10.1002/chem.201103784,10.1055/s-0031-1289687,10.1021/ja207759e,10.1002/anie.201101461Kelly11/25/2021
91
142FALSEchem.20110298410.1002/chem.201102984https://sci-hub.wf/10.1002/chem.201102984https://doi.org/10.1002/chem.201102984NiC-O ActivationKellyTRUE80912012Gong, HG
Ni-Catalyzed Reductive Allylation of Unactivated Alkyl Halides with Allylic Carbonates
CHEMISTRY-A EUROPEAN JOURNAL
Shanghai Univ1/16/2012Csp3-Csp3E-EOX
OCO2Me
IAllylAlkyl#N/ANo BaseMedium0.31_xxx10.1021/ol502682q,10.1021/ol3011198,10.1039/c3ob40232k,10.1021/jacs.0c01330,10.1039/c2cc33232a,10.1002/anie.201705521,10.1039/d1cc02837e,10.1039/c5cc03113c,10.1021/ol301334210.1002/ejic.202100820,10.6023/cjoc202106021,10.1021/acs.orglett.1c03298,10.1021/jacs.1c08695,10.1021/acs.orglett.1c02938,10.1021/acs.orglett.1c02616,10.1039/d1cc02837e,10.1039/d1sc01115d,10.1021/acs.orglett.1c00058,10.1039/d0cs00262c,10.1002/anie.202006293,10.1021/acs.accounts.0c00032,10.1021/jacs.0c01330,10.1039/c9cc07072a,10.1002/anie.201909543,10.1016/j.tet.2019.06.034,10.1039/c9qo00562e,10.1021/acs.orglett.9b01987,10.3390/molecules24081458,10.1039/c9ob00111e,10.1021/acs.orglett.8b00235,10.1016/bs.aihch.2017.10.001,10.1021/acs.organomet.7b00613,10.1002/anie.201705521,10.1002/cjoc.201700071,10.1002/anie.201702857,10.1021/acs.orglett.7b00473,10.1021/acs.joc.6b02830,10.1021/jacs.6b10350,10.1021/jacs.6b06862,10.1055/s-0035-1562442,10.1021/acs.orglett.6b01837,10.1007/s41061-016-0042-2,10.1039/c6dt02185a,10.1055/s-0035-1560324,10.1055/s-0035-1560531,10.1021/jacs.5b06255,10.1002/chem.201501543,10.1002/adsc.201400970,10.1039/c5ob01901j,10.1039/c4cc08703h,10.1039/c5cc03113c,10.1039/c5qo00224a,10.1002/tcr.201402058,10.1021/ol502682q,10.1021/ja508067c,10.1055/s-0033-1339111,10.1055/s-0033-1339126,10.1021/jo500507s,10.1002/chem.201402302,10.1021/ja5024749,10.1002/ejic.201301115,10.1055/s-0033-1340151,10.1039/c4ob00642a,10.1080/00397911.2014.924141,10.1039/c3cc49859j,10.1039/c4ob00403e,10.1055/s-0033-1339435,10.1016/j.tetlet.2013.07.043,10.1021/ja4030462,10.1055/s-0032-1318237,10.1021/ja309176h,10.1039/c3cc42292e,10.1039/c3sc51098k,10.1039/c3ob40232k,10.1021/ol3013342,10.1021/ol3011198,10.1002/chem.201200190,10.1002/ejoc.201101842,10.1039/c2cc33232aKelly1/11/2022
92
94FALSEchem.20110305010.1002/chem.201103050https://sci-hub.wf/10.1002/chem.201103050https://doi.org/10.1002/chem.201103050NiC-O ActivationGerryTRUE49322012Jin, Z
Biphenyl-Based Diaminophosphine Oxides as Air-Stable Preligands for the Nickel-Catalyzed Kumada-Tamao-Corriu Coupling of Deactivated Aryl Chlorides, Fluorides, and Tosylates
CHEMISTRY-A EUROPEAN JOURNAL
Nankai Univ1/9/2012Csp2_ar-Csp2_arE-NuOMgOTsMgXArylArylNo baseNo BaseWeak0.36_10.1021/acs.organomet.5b00874,10.1016/j.tet.2017.06.004,10.1021/acscatal.7b0105810.3390/molecules26226968,10.1039/d1cc04189d,10.1021/acs.orglett.0c02609,10.1021/acs.orglett.9b02858,10.1039/c9cy01501a,10.1021/acs.joc.9b00708,10.1002/ejic.201801477,10.1007/s00706-019-2364-6,10.1016/j.tet.2018.10.025,10.1021/acs.orglett.8b02351,10.1002/celc.201800422,10.1007/s11426-018-9333-x,10.1039/c8dt01295d,10.1021/acscatal.8b01224,10.1002/adsc.201701506,10.1016/j.tet.2017.06.004,10.1021/acscatal.7b01058,10.1021/acs.organomet.7b00129,10.1021/acs.joc.6b02354,10.1021/acs.joc.6b01041,10.1002/pi.5086,10.1002/hc.21309,10.1007/s40242-016-5261-0,10.2533/chimia.2016.8,10.1039/c5nj01833a,10.1039/c6cc07199f,10.1021/acs.organomet.5b00874,10.1021/acscatal.5b01463,10.6023/cjoc201409007,10.1021/cr500257c,10.1002/chem.201405275,10.1016/j.tetlet.2014.11.020,10.1021/jo5022234,10.1002/anie.201402695,10.1021/jo500619f,10.1002/chem.201303809,10.1039/c3dt52985a,10.1039/c4ob01041h,10.1016/j.jorganchem.2013.06.033,10.1021/ja406730t,10.1002/ejoc.201300850,10.1016/j.jorganchem.2013.03.021,10.1021/ja404006w,10.1002/chem.201202950,10.1021/jo302425x,10.1039/c3ra44884c,10.1002/chem.201200305Kelly2/15/2022
93
99FALSEc1cc16582h10.1039/c1cc16582hhttps://sci-hub.wf/10.1039/c1cc16582hhttps://doi.org/10.1039/c1cc16582hNiC-H ActivationElaineFALSE354892012Chatani, N#N/ARegioselective C-H bond functionalizations of acridines using organozinc reagents
CHEM COMMUN
Despite the recent advance in C-H bond functionalization chemistry, the C-H bonds in the acridine ring system, which is an important scaffold in medicinal and material science, have met with limited success, due, in part, to the lack of activated C-H bonds adjacent to the ring nitrogen atom. Herein, several protocols that can effect the regioselective arylation and alkylation of acridines at the C-4 and C-9 positions are described.
Osaka Univ7/4/2012TRUEFALSEFALSE_10.1021/ja306062c,10.1021/ja413131m,10.1002/asia.201100971,10.1021/ja401344e10.1016/j.tet.2020.131435,10.1021/acs.joc.0c00137,10.1007/s10593-019-02562-x,10.1021/acs.chemrev.9b00047,10.1021/acs.chemrev.8b00507,10.1246/cl.180857,10.3390/molecules23112867,10.1016/j.ica.2018.03.036,10.6023/cjoc201710007,10.1039/c7cc06958h,10.1002/adsc.201700715,10.1021/acs.chemrev.7b00021,10.1002/ejoc.201601553,10.1007/s41061-016-0053-z,10.1039/c6ra17783b,10.1002/bkcs.10629,10.1002/chem.201500290,10.1016/j.tet.2015.03.066,10.1021/om501251q,10.1021/om501239n,10.3987/COM-14-S(K)7,10.1016/bs.aihch.2015.04.004,10.1021/jo5020432,10.1002/chem.201403356,10.1021/ja413131m,10.1021/ja409803x,10.1021/ja406131a,10.1021/ja401344e,10.1002/anie.201208666,10.1002/ejoc.201200914,10.1021/jo301618b,10.1021/ja306062c,10.1002/asia.201100971#N/A2012FALSEFALSEFALSEFALSE482308
94
166FALSEchem.20110378410.1002/chem.201103784https://sci-hub.wf/10.1002/chem.201103784https://doi.org/10.1002/chem.201103784NiC-O ActivationLongTRUE8716252012Wang, C
Aryl Ether as a Negishi Coupling Partner: An Approach for Constructing C-C Bonds under Mild Conditions
CHEMISTRY-A EUROPEAN JOURNAL
RIKEN3/1/2012FALSEFALSECsp2_ar-Csp2_arE-NuOZnOMe
ZnMe3Li2
ArylArylNo baseNo BaseStrong-0.28_xAdded by Long10.1002/chem.201603436,10.1021/ja307045r,10.1021/acs.orglett.5b02200,10.1021/acscatal.9b00744,10.1021/acscatal.8b03436,10.1039/c4cc08187k,10.1021/acscatal.7b01058,10.1021/ol4031815,10.1002/anie.201402922,10.1002/anie.201510497,10.1246/cl.150936,10.1021/jacs.6b03253,10.1016/j.tet.2012.04.005,10.1021/ol502583h,10.1002/anie.201607646,10.1021/ol503707m10.1002/aoc.6430,10.1039/d1nj03706d,10.1021/jacs.1c03038,10.1055/a-1467-2494,10.1021/acs.joc.0c02389,10.1055/a-1349-3543,10.1021/acs.orglett.0c03507,10.1002/chem.202004132,10.1021/acs.chemrev.0c00088,10.1248/cpb.c20-00196,10.1002/cjoc.201900506,10.1246/cl.200083,10.1002/jccs.201900450,10.1002/adsc.201900745,10.1021/acscatal.9b00744,10.1007/3418_2018_19,10.1021/acscatal.8b03436,10.1002/ajoc.201800560,10.1016/j.tet.2018.10.025,10.1039/c8cc03665a,10.1021/acscatal.8b01224,10.1038/s41467-018-03928-z,10.1039/c7cc08709h,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.1002/chem.201703266,10.1055/s-0036-1590985,10.1021/acs.organomet.7b00632,10.1248/cpb.c17-00487,10.1021/acscatal.7b01058,10.1021/acs.orglett.7b00447,10.1021/acscatal.6b02964,10.1002/anie.201607646,10.1002/ajoc.201600411,10.1002/chem.201603436,10.1002/asia.201600972,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1248/yakushi.15-00294,10.1021/jacs.6b03253,10.1002/anie.201510497,10.1021/acscatal.5b02058,10.1016/bs.adomc.2016.07.001,10.1021/acs.joc.5b02151,10.1246/cl.150936,10.1021/jacs.5b08621,10.1111/cas.12813,10.1002/ejoc.201500987,10.1002/chem.201502114,10.1021/acs.orglett.5b02200,10.1002/chem.201501811,10.1021/acs.orglett.5b01229,10.1016/j.tet.2015.02.088,10.1002/asia.201500308,10.1021/acs.accounts.5b00051,10.1021/acs.orglett.5b00654,10.1246/cl.141084,10.1021/ol503707m,10.1039/c5qo00001g,10.1039/c5qo00039d,10.1039/c5sc00305a,10.1039/c4cc08187k,10.1039/c4cc10084k,10.1016/S1872-2067(14)60217-5,10.1002/anie.201402922,10.1021/ol502583h,10.1002/chem.201404380,10.1016/j.tet.2014.04.052,10.1021/jo500619f,10.1002/chem.201303809,10.1021/ja410883p,10.1039/c4cs00206g,10.1007/3418_2013_72,10.1021/ol4031815,10.1021/ja409748m,10.1002/cctc.201300177,10.1002/anie.201302448,10.1021/ja311940s,10.1002/ajoc.201200185,10.1021/ja307045r,10.1016/j.tet.2012.04.005Kelly12/22/2021
95
80FALSEchem.20150232910.1002/chem.201502329https://sci-hub.wf/10.1002/chem.201502329https://doi.org/10.1002/chem.201502329NiC-O ActivationGerry14-FebTRUE518632015
Carpentier, JF
Pentacoordinated Carboxylate pi-Allyl Nickel Complexes as Key Intermediates for the Ni-Catalyzed Direct Amination of Allylic Alcohols
CHEMISTRY-A EUROPEAN JOURNAL
Direct amination of allylic alcohols with primary and secondary amines catalyzed by a system made of [Ni(1,5-cyclooctadiene)(2)] and 1,1'-bis(diphenylphosphino)-ferrocene was effectively enhanced by adding nBu(4)NOAc and molecular sieves, affording the corresponding allyl amines in high yield with high monoallylation selectivity for primary amines and high regioselectivity for monosubstituted allylic alcohols. Such remarkable additive effects of nBu(4)NOAc were elucidated by isolating and characterizing some nickel complexes, manifesting the key role of a charge neutral pentacoordinated eta(3)-allyl acetate complex in the present system, in contrast to usual cationic tetracoordinated complexes earlier reported in allylic substitution reactions.
Univ Rennes 110/5/2015Csp3-Nsp3E-NuOHOHHAllyl
N(Alkyl)Alkyl
No baseNo BaseStrong-0.81_10.1002/anie.201508757,10.1021/acscatal.1c01626,10.1002/anie.201703486,10.1039/c7sc03140h,10.1021/acscatal.0c01356,10.1021/jacs.1c11044,10.1021/acscatal.7b03079,10.1002/anie.20180561110.1021/jacs.1c11044,10.1002/ejic.202100820,10.1002/chem.202103093,10.1021/acscatal.1c03729,10.1021/acs.orglett.1c02893,10.1021/acs.joc.1c01930,10.1021/acscatal.1c03449,10.6023/cjoc202104030,10.1021/acs.orglett.1c02406,10.1021/acscatal.1c01626,10.1021/acs.chemrev.0c01115,10.1002/adsc.202001338,10.1021/acs.chemrev.9b00682,10.1002/ejoc.202000413,10.1021/acscatal.0c01356,10.1002/anie.202000704,10.1039/c9gc03619a,10.1021/acs.orglett.9b03633,10.1021/jacs.9b07253,10.1002/chem.201805987,10.1002/cctc.201801841,10.1055/s-0037-1612010,10.6023/cjoc201809037,10.1002/cjoc.201800237,10.1002/chem.201801492,10.1021/acs.joc.8b01474,10.1002/anie.201805611,10.1002/chem.201800348,10.1002/chem.201801241,10.1002/ajoc.201800083,10.1039/c7sc03140h,10.1021/acscatal.7b03079,10.1021/acs.orglett.7b03023,10.1002/ejoc.201700486,10.1002/anie.201703486,10.1021/acs.orglett.7b01208,10.6023/cjoc201702013,10.6023/cjoc201610034,10.1002/chem.201700909,10.1002/ejoc.201601311,10.1002/chem.201605611,10.1002/ejoc.201600500,10.1248/cpb.c16-00282,10.1002/chem.201505214,10.1002/anie.2015087572/14/2022
96
81FALSEchem.20150510610.1002/chem.201505106https://sci-hub.wf/10.1002/chem.201505106https://doi.org/10.1002/chem.201505106NiC-O ActivationLongTRUE4721162016Feringa, BL
Nickel-Catalyzed Cross-Coupling of Organolithium Reagents with (Hetero)Aryl Electrophiles
CHEMISTRY-A EUROPEAN JOURNAL
Nickel-catalyzed selective cross-coupling of aromatic electrophiles (bromides, chlorides, fluorides and methyl ethers) with organolithium reagents is presented. The use of a commercially available nickel N-heterocyclic carbene (NHC) complex allows the reaction with a variety of (hetero)aryllithium compounds, including those prepared via metal-halogen exchange or direct metallation, whereas a commercially available electron-rich nickel-bisphosphine complex smoothly converts alkyllithium species into the corresponding coupled product. These reactions proceed rapidly (1h) under mild conditions (room temperature) while avoiding the undesired formation of reduced or homocoupled products.
Univ Groningen3/14/2016Csp2_ar-Csp2_arE-NuOLiOMeLiArylArylNo baseNo BaseStrong-0.28_10.1021/jacs.7b04279,10.1002/chem.20160343610.1002/anie.202110785,10.1021/acscatal.1c03564,10.1002/tcr.202100204,10.1039/d1cc02762j,10.1039/d1qo00549a,10.1002/tcr.202100053,10.1039/d0ob02491k,10.1055/a-1349-3543,10.1021/acs.orglett.0c03507,10.1021/acs.chemrev.0c00088,10.1002/anie.202008866,10.1021/acs.orglett.0c02609,10.1002/anie.201913132,10.1021/acscatal.9b02316,10.1002/adsc.201801713,10.1002/adsc.201801586,10.1021/acs.orglett.9b00394,10.1039/c8ob02977f,10.1002/anie.201812537,10.1007/3418_2019_28,10.1007/3418_2018_19,10.1002/ejoc.201801286,10.1055/s-0037-1609941,10.1002/anie.201707760,10.1002/anie.201804479,10.1002/chem.201800118,10.1021/acs.joc.8b00510,10.1038/s41467-018-03928-z,10.1002/adsc.201701506,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.1021/acs.joc.7b02004,10.1002/ejoc.201701005,10.1248/cpb.c17-00487,10.1021/jacs.7b04279,10.1016/j.crci.2017.01.006,10.1002/anie.201700417,10.1021/acs.organomet.6b00769,10.1021/acs.joc.6b02666,10.1002/adsc.201600887,10.1002/chem.201603436,10.1007/s41061-016-0043-1,10.1002/chem.201601911,10.1016/bs.adomc.2016.07.0011/6/2022
97
113FALSEchem.20160132010.1002/chem.201601320https://sci-hub.wf/10.1002/chem.201601320https://doi.org/10.1002/chem.201601320NiC-O ActivationGerryTRUE567382016Weix, DJ
Cross-Electrophile Coupling of Vinyl Halides with Alkyl Halides
CHEMISTRY-A EUROPEAN JOURNAL
An improved method for the reductive coupling of aryl and vinyl bromides with alkyl halides that gave high yields for a variety of substrates at room temperature with a low (2.5 to 0.5 mol%) catalyst loading is presented. Under the optimized conditions, difficult substrates, such as unhindered alkenyl bromides, can be coupled to give the desired olefins with minimal diene formation and good stereoretention. These improved conditions also worked well for aryl bromides. For example, a gram-scale reaction was demonstrated with 0.5 mol% catalyst loading, whereas reactions at 10 mol% catalyst loading completed in as little as 20 minutes. Finally, a low-cost single-component pre-catalyst, (bpy)NiI2 (bpy=2,2'-bipyridine) that is both air-and moisture-stable over a period of months was introduced.
Univ Rochester5/23/2016Csp3-Csp2E-EOXOTfBrAlkylVinylNo baseNo BaseWeak0.53_10.1021/acs.orglett.7b00831,10.1002/anie.202114556,10.1039/c9sc03347e,10.1021/jacs.7b13601,10.1055/s-0037-1610084,10.1021/jacs.9b05224,10.1021/jacs.9b0546110.1039/d2ra00010e,10.1002/anie.202114556,10.1039/d1qo01219c,10.1021/acscatal.1c03265,10.1021/acs.orglett.1c02887,10.1055/a-1650-8519,10.1002/anie.202107492,10.1021/jacs.1c05281,10.1039/d1nj01732b,10.1002/anie.202100288,10.1055/s-0040-1707342,10.1002/anie.202010737,10.1021/acscatal.0c03237,10.1055/s-0040-1707885,10.1055/s-0040-1707127,10.1021/acscatal.0c01842,10.1021/acs.chemrev.9b00682,10.1021/acs.oprd.0c00134,10.1021/jacs.0c02673,10.1021/acs.orglett.0c00561,10.1002/anie.201914215,10.1021/acs.orglett.9b04320,10.7536/PC190809,10.1039/c9sc03347e,10.1021/jacs.9b05224,10.1021/acs.oprd.9b00232,10.1021/jacs.9b05461,10.1039/c9cc00768g,10.1021/jacs.9b03978,10.6023/cjoc201806038,10.1002/ajoc.201800625,10.1021/acs.orglett.8b02222,10.1055/s-0037-1610084,10.1021/acs.joc.8b00882,10.1021/jacs.8b04637,10.1002/anie.201713278,10.1021/jacs.7b13601,10.1021/acs.orglett.8b00114,10.1021/jacs.7b12212,10.1055/s-0036-1591853,10.1016/bs.aihch.2017.10.001,10.1002/anie.201706781,10.1055/s-0036-1588464,10.1021/acs.joc.7b01334,10.1021/acs.orglett.7b01513,10.1021/acs.orglett.7b00831,10.1021/jacs.7b01705,10.1021/acs.orglett.7b00793,10.1055/s-0036-1588132,10.1002/chem.201603832,10.1002/anie.201607959,10.1002/chem.201602668,10.1039/c6ob02269cKelly1/20/2022
98
75FALSEchem.20160343610.1002/chem.201603436https://sci-hub.wf/10.1002/chem.201603436https://doi.org/10.1002/chem.201603436NiC-O ActivationLongTRUE46342016Uchiyama, M
Cross-Coupling of Organolithium with Ethers or Aryl Ammonium Salts by C-O or C-N Bond Cleavage
CHEMISTRY-A EUROPEAN JOURNAL
Various aryl-, alkenyl-, and/or alkyllithium species reacted smoothly with aryl and/or benzyl ethers with cleavage of the inert C-O bond to afford cross-coupled products, catalyzed by commercially available [Ni(cod)(2)] (cod=1,5-cyclooctadiene) catalysts with N-heterocyclic carbene (NHC) ligands. Furthermore, the coupling reaction between the aryllithium compounds and aryl ammonium salts proceeded under mild conditions with C-N bond cleavage in the presence of a [Pd(PPh3)(2)Cl-2] catalyst. These methods enable selective sequential functionalizations of arenes having both C-N and C-O bonds in one pot.
Univ Tokyo10/24/2016TRUEFALSECsp2_ar-Csp2_arE-NuOLiOMeLiArylArylNo baseNo BaseStrong-0.28_xxAdded by Long10.1021/acscatal.8b03436,10.1021/acscatal.7b01058,10.1002/anie.20180679010.1002/anie.202110785,10.1021/acscatal.1c03564,10.1016/j.tet.2021.132431,10.1039/d1ob01468d,10.1039/d1qo00759a,10.1002/tcr.202100089,10.1055/a-1509-5954,10.1021/jacs.1c03038,10.1021/acs.joc.0c02992,10.1055/a-1349-3543,10.1021/acs.orglett.0c03507,10.1021/acscatal.0c03341,10.1021/acs.chemrev.0c00088,10.1002/asia.202000763,10.1248/cpb.c20-00196,10.1039/d0ob00956c,10.1039/d0sc01585g,10.1002/cjoc.201900506,10.1246/cl.200083,10.1039/c9ob02667c,10.1039/c9ob02107h,10.1021/acs.joc.9b01113,10.1002/adsc.201801713,10.1002/chem.201900886,10.1021/acscatal.9b00218,10.1038/s41929-019-0250-6,10.1007/3418_2018_19,10.1021/acscatal.8b03436,10.6023/cjoc201803013,10.1002/anie.201806790,10.1039/c8ob00488a,10.1038/s41467-018-03928-z,10.1002/anie.201712618,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.1002/asia.201701342,10.1021/jacs.7b08579,10.1002/asia.201701132,10.1021/acscatal.7b02025,10.1248/cpb.c17-00487,10.1021/acscatal.7b01058,10.1021/acscatal.6b02964 Long 11/9/2021
99
105FALSEom500452c10.1021/om500452chttps://sci-hub.wf/10.1021/om500452chttps://doi.org/10.1021/om500452cNiC-N ActivationShihongTRUE36452014Wang, ZX
Mono- and Dinuclear Pincer Nickel Catalyzed Activation and Transformation of C-Cl, C-N, and C-O Bonds
ORGANOMETALLICS
Condensation of 2-NH2C6H4P(Et)Ph (2) with pyrrole-2-carboxaldehyde generated 2-(C4H4N-2'-CH-N)C6H4P(Et)Ph (3). Treatment of 3 with NaH and followed by (DME)NiX2 (X = Cl, Br) afforded mononuclear pincer nickel complexes [Ni{2-(C4H3N-2'-CH-N)C6H4P(Et)Ph}X] (4a, X = Cl; 4b, X = Br). Reaction of [2-NH2C6H4P(Ph)](2)(CH2)(n) (5a, n = 3; 5b, n = 4) with pyrrole-2-carboxaldehyde or 5-tert-butyl-1H-pyrrole-2-carbaldehyde formed [2-(C4H4N-2'-CH-N)C6H4P(Ph)](2)(CH2)(n) (6a, n = 3; 6b, n = 4) and [2-(5'-tBuC(4)H(3)N-2'-CH-N)C6H4P(Ph)](2)(CH2)(4) (6c). Respective treatment of 6ac with NaH followed by (DME)NiX2 (X = Cl, Br) gave the dinuclear nickel complexes [Ni{2-(5'-RC4H2N-2'-CH-N)C6H4P(Ph)}X](2)(CH2)(n) (7a, R = H, X = Cl, n = 3; 7b, R = H, X = Cl, n = 4; 7c, R = H, X = Br, n = 4; 7d, R = tBu, X = Cl, n = 4). Catalysis of the complexes for the activation and transformation of CCl, CN, and CO bonds was evaluated. Complex 7c exhibited excellent catalytic activity in the cross-coupling of aryl chlorides or aryltrimethylammonium iodides with arylzinc reagents as well as of aryl sulfamates with aryl Grignard reagents. The dinuclear nickel complexes 7bd showed higher catalytic activity than the mononuclear complexes in each type of reaction.
Univ Sci & Technol China
10/27/2014Csp2_ar-Csp2_arE-NuNZn
NMe3+I-
ZnXArylArylNo baseNo BaseE-H_10.1039/c4qo00321g,10.1016/j.tet.2017.06.004,10.1002/anie.201511197,10.1021/acs.organomet.5b0087410.1016/j.fuel.2021.121377,10.1039/d1qo00759a,10.1021/acs.joc.0c02389,10.1002/ejic.202000721,10.1021/acs.joc.0c01274,10.1039/d0qo00173b,10.1016/j.jinorgbio.2020.111015,10.1039/c9ob02667c,10.1021/acs.inorgchem.9b02539,10.1002/ejic.201801179,10.3866/PKU.WHXB201807071,10.1039/c8dt03210f,10.6023/cjoc201803013,10.1002/asia.201701342,10.1021/acs.orglett.7b03145,10.1002/ijch.201700044,10.1002/asia.201701132,10.1021/acs.inorgchem.7b01616,10.1016/j.tet.2017.06.004,10.1007/s00894-017-3387-8,10.1039/c7qo00174f,10.1039/c6qo00670a,10.1039/c7ra02549a,10.1002/ajoc.201600045,10.1002/adsc.201500743,10.1002/anie.201511197,10.1021/acs.joc.5b02557,10.1021/acs.organomet.5b00874,10.1021/acs.joc.5b02151,10.1002/chem.201503596,10.1002/anie.201508161,10.1021/acs.orglett.5b02458,10.1002/ejoc.201500987,10.6023/cjoc201503014,10.1039/c4qo00321g,10.1039/c5ra16782eLong1/5/2022
100
296FALSEchem.20160445210.1002/chem.201604452https://sci-hub.wf/10.1002/chem.201604452https://doi.org/10.1002/chem.201604452NiC-O ActivationxWilliam11-JunTRUE711892016Rueping, M
Decarboxylative Aminomethylation of Aryl- and Vinylsulfonates through Combined Nickel- and Photoredox-Catalyzed Cross-Coupling
CHEMISTRY-A EUROPEAN JOURNAL
A mild approach for the decarboxylative aminomethylation of aryl sulfonates by the combination of photoredox and nickel catalysis through C-O bond cleavage is described for the first time. A wide range of aryl triflates as well as aryl mesylates, tosylates and alkenyl triflates afford the corresponding products in good to excellent yields.
1/11/2016Csp2_ar-Nsp3E-EOCsp2OTfCOOHAryl
N(H)Alkyl
Cs2CO3Ionic-CO3Weak0.536/15/2022
101
48FALSEchem.20160509510.1002/chem.201605095https://sci-hub.wf/10.1002/chem.201605095https://doi.org/10.1002/chem.201605095NiC-O ActivationKellyTRUE357382016
Stradiotto, M
Nickel-Catalyzed N-Arylation of Primary Amides and Lactams with Activated (Hetero)aryl Electrophiles
CHEMISTRY-A EUROPEAN JOURNAL
The first nickel-catalyzed N-arylation of amides with (hetero) aryl (pseudo) halides is reported, enabled by use of the air-stable pre-catalyst (PAd-DalPhos) Ni(o-tolyl)Cl(C1). A range of structurally diverse primary amides and lactams were cross-coupled successfully with activated (hetero) aryl chloride, bromide, triflate, tosylate, mesylate, and sulfamate electrophiles.
Dalhousie Univ12/23/2016Csp2_ar-Nsp3E-NuOHOTfHAryl
N(H)Alkyl
Ionic-OtBuWeak0.53_x10.1002/anie.202002392,10.1021/acscatal.1c03010,10.1021/acscatal.7b02014,10.1002/anie.202014340,10.1021/acscatal.0c00393,10.1021/acscatal.8b01879,10.1021/jacs.8b0180010.1021/acscatal.1c05386,10.1002/slct.202103723,10.1021/acscatal.1c05386,10.2174/1570178618666210125161436,10.1021/acscatal.1c04538,10.1021/acscatal.1c03010,10.1039/d0qo01194k,10.1002/anie.202014340,10.1021/acscatal.0c03888,10.1055/a-1337-6459,10.1021/acs.joc.0c02157,10.1039/d0nj01610a,10.1021/acscatal.0c00393,10.1002/anie.202002392,10.1021/acs.organomet.9b00561,10.1021/acs.orglett.9b03274,10.1021/acscatal.9b03715,10.1021/acs.orglett.9b02621,10.1055/s-0037-1611732,10.1002/anie.201900095,10.1021/jacs.9b01886,10.1002/anie.201812862,10.1021/acs.organomet.8b00451,10.1021/acs.organomet.8b00605,10.1021/acscatal.8b01879,10.1021/acscatal.8b01005,10.1021/acs.joc.8b00160,10.1021/jacs.8b01800,10.1021/acs.orglett.7b02326,10.1002/adsc.201700672,10.1021/acscatal.7b02014,10.1021/acs.joc.7b01215,10.1055/s-0036-1588806,10.1055/s-0036-1590819,10.1002/ajoc.201600596,10.1021/acs.organomet.6b008852/15/2022
102
108FALSEc1cc14558d10.1039/c1cc14558dhttps://sci-hub.wf/10.1039/c1cc14558dhttps://doi.org/10.1039/c1cc14558dNiC-H ActivationGerryTRUE382#N/A2011Qu, GR
Nickel-catalyzed sp(2) C-H bonds arylation of N-aromatic heterocycles with Grignard reagents at room temperature
CHEM COMMUN
A novel protocol for nickel-catalyzed direct sp(2) C-H bond arylation of purines has been developed. This new reaction proceeded efficiently at room temperature using Grignard reagent as the coupling partner within 5 hours in good to high yields. This approach provides a new access to a variety of C8-arylpurines which are potentially of great importance in medicinal chemistry.
Henan Normal Univ9/6/2011yCsp2_ar-Csp2_arNu-NuMgHMgXHArylHetNo baseNo BaseNu-M_x10.1021/ja413131m,10.1021/ja401344e10.1002/tcr.202100113,10.1002/adsc.202001498,10.1016/j.chempr.2020.04.005,10.1002/ajoc.201900069,10.1039/c9qo00039a,10.1021/acs.chemrev.8b00507,10.1002/cssc.201700321,10.1002/anie.201606529,10.1007/s41061-016-0053-z,10.1016/j.tet.2016.02.037,10.1016/bs.aihch.2016.04.005,10.1002/adsc.201500799,10.1002/adsc.201500314,10.6023/cjoc201411040,10.1039/c5ra04406e,10.3998/ark.5550190.p008.915,10.1039/c4cc09844g,10.1002/chem.201403356,10.1021/ja413131m,10.1021/jo402248d,10.1021/ol402644y,10.1039/c3ob41488d,10.1016/j.tet.2013.05.135,10.1021/ja401344e,10.1002/ejoc.201200914,10.1021/ol302640e,10.1002/ajoc.201200081,10.1021/ol301848v,10.1021/ol300570f,10.1039/c2ra20366a,10.1039/c2cs35096c12/29/2021
103
109FALSEc4qo00321g10.1039/c4qo00321ghttps://sci-hub.wf/10.1039/c4qo00321ghttps://doi.org/10.1039/c4qo00321gNiC-N ActivationShihongTRUE392#N/A2015Wu, D
Highly efficient pincer nickel catalyzed cross-coupling of aryltrimethylammonium triflates with arylzinc reagents
ORG CHEM FRONT
N,N,P-Pincer-nickel-complex-catalyzed cross-coupling of aryltrimethylammonium triflates with aryl- or heteroaryl-zinc reagents was investigated. The reaction is suitable for a broad scope of substrates, exhibits good functional group compatibility and can be performed under mild conditions with extremely low catalyst loadings.
Univ Sci & Technol China
1/22/2015Csp2_ar-Csp2_arE-NuNZn
NMe3+OTf-
ZnXArylArylNo baseNo BaseE-H_10.1002/anie.201511197,10.1039/c6ob01299j10.1177/17475198211063806,10.1016/j.tet.2021.132431,10.1039/d1ob01468d,10.1039/d1qo00759a,10.1021/acs.joc.0c02992,10.1021/acscatal.0c03341,10.1039/c9ob02667c,10.1039/c9ob02107h,10.1021/acs.orglett.9b02820,10.1021/acscatal.9b00218,10.1021/acs.joc.8b02926,10.6023/cjoc201809037,10.1002/ejic.201801179,10.1021/jacs.8b08792,10.1002/ajoc.201800560,10.1039/c8ob00488a,10.1002/asia.201701342,10.1021/acs.orglett.7b03145,10.1002/ijch.201700044,10.3184/174751917X15094552081206,10.1002/asia.201701132,10.1002/asia.201700313,10.1039/c7qo00174f,10.1039/c7ra02549a,10.1016/j.tet.2016.10.018,10.1016/j.tetlet.2016.02.097,10.1002/ajoc.201600045,10.1002/anie.201511197,10.1039/c6cc06089g,10.1039/c6ob01299j,10.1039/c6cc04531f,10.1021/acs.joc.5b02557,10.1021/acs.joc.5b02151,10.1002/chem.201503596,10.1021/acs.orglett.5b02458,10.1002/ejoc.201500987Long12/22/2021
104
57FALSEcssc.20180144310.1002/cssc.201801443https://sci-hub.wf/10.1002/cssc.201801443https://doi.org/10.1002/cssc.201801443NiC-O ActivationShihong9-FebTRUE372332018Balaraman, E
Ni-Catalyzed alpha-Alkylation of Unactivated Amides and Esters with Alcohols by Hydrogen Auto-Transfer StrategyCHEMSUSCHEM
A transition-metal-catalyzed borrowing hydrogen/hydrogen auto-transfer strategy allows the utilization of feedstock alcohols as an alkylating partner, which avoids the formation of stoichiometric salt waste and enables a direct and benign approach for the construction of C-N and C-C bonds. In this study, a nickel-catalyzed alpha-alkylation of unactivated amides and ester (tert-butyl acetate) is carried out by using primary alcohols under mild conditions. This C-C bond-forming reaction is catalyzed by a new, molecularly defined nickel(II) NNN-pincer complex (0.1-1 mol %) and proceeds through hydrogen auto-transfer, thereby releasing water as the sole byproduct. In addition, N-alkylation of cyclic amides under Ni-catalytic conditions is demonstrated.
CSIR11/23/2018Csp3-ring(s)-Csp3E-NuOHOHHBenzylAlkylKOtBuIonic-OtBuStrong-0.81_10.1021/acs.joc.8b02609,10.1039/d0cc06468h10.3390/molecules26216374,10.1002/aoc.6493,10.1002/adsc.202101077,10.1002/tcr.202100165,10.1021/acs.organomet.1c00328,10.1039/d1ob01154e,10.1038/s41598-021-89561-1,10.1039/d1nj01581h,10.1039/d1dt01206a,10.1021/acscentsci.1c00125,10.1039/d1ob00080b,10.1039/d0dt03593a,10.1021/acs.organomet.1c00009,10.1016/j.ica.2020.120182,10.1002/ajoc.202000634,10.1039/d0gc02341h,10.1039/d0cc06468h,10.1007/s40010-020-00722-9,10.1021/acs.orglett.0c02635,10.1039/d0sc02948c,10.3390/catal10080861,10.1002/ejoc.202000296,10.1021/acs.organomet.0c00233,10.1021/acs.joc.0c00561,10.1002/cssc.202000576,10.1021/acs.joc.9b03104,10.1021/acs.orglett.9b02990,10.1002/ejoc.201901310,10.1002/cctc.201901319,10.1002/ajoc.201900438,10.1002/asia.201900908,10.1002/cssc.201900799,10.1039/c9cc02603g,10.1039/c9ob00418a,10.1021/acsomega.9b00567,10.1021/acs.joc.8b026091/5/2022
105
23FALSEejic.20190069210.1002/ejic.201900692https://sci-hub.wf/10.1002/ejic.201900692https://doi.org/10.1002/ejic.201900692NiC-O ActivationGerryTRUE121242019Ong, TG
Nickel Carbodicarbene Catalyzes Kumada Cross-Coupling of Aryl Ethers with Grignard Reagents through C-O Bond Activation
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
The development of a cross-coupling reaction protocol between aryl ethers and Grignard reagents catalyzed by carbodicarbene (CDC) nickel complexes to afford biaryl compounds through C-O cleavage is reported. Aromatic substrates featuring a broad range of electron neutral, donating, or withdrawing groups are introduced at the desired position. The method has proven effective over a wide range of naphthyl methyl ethers, anisoles, and Grignard reagents. The robustness of the protocol is validated by performing multiple cleavage reactions, gram scale synthesis, and arylation of a dimethoxy esterdiol derivative.
Acad Sinica8/15/2019yCsp2_ar-Csp2_arE-NuOMgOMeMgXArylArylNo baseNo BaseStrong-0.28_xx10.1021/acsomega.1c06430,10.1002/ejoc.202100866,10.1002/anie.202107127,10.1002/zaac.202100151,10.1055/a-1509-5954,10.1021/jacs.1c03038,10.1039/d0dt03942j,10.1055/a-1349-3543,10.1039/d0ra07472a,10.1021/acs.inorgchem.0c001532/8/2022
106
218FALSEejoc.20090006710.1002/ejoc.200900067https://sci-hub.wf/10.1002/ejoc.200900067https://doi.org/10.1002/ejoc.200900067NiC-O ActivationLongTRUE14015242009Inamoto, K
N-Heterocyclic Carbene Derived Nickel-Pincer Complexes: Efficient and Applicable Catalysts for Suzuki-Miyaura Coupling Reactions of Aryl/Alkenyl Tosylates and Mesylates
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Catalytic activities of NHC-derived nickel-pincer complexes for the Suzuki-Miyaura coupling reactions of aryl/alkenyl to-sylates and mesylates are described. In the presence of a catalytic amount of nickelacycle 1a, a wide array of tosylates and mesylates reacted with several aryl- and alkenylboronic acids to afford the coupling products, generally in high yields. Fine tuning of the reaction conditions for each class of electrophiles was achieved only by choosing the appropriate reaction medium (DME for tosylates, dioxane for mesylates). ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Tohoku Univ5/1/2009Csp2_ar-Csp2_arE-NuOBOTsB(OH)2ArylArylK3PO4Ionic-PO4Weak0.36_x10.1021/jo202037x,10.1021/jo2022982,10.1021/jo501291y,10.1002/ejoc.201000147,10.1002/chem.201003403,10.1021/ol403209k,10.1002/ejoc.201001519,10.1021/ol101592r,10.1039/c0cc03107k,10.1002/ejoc.201200444,10.1002/adsc.201100151,10.1021/jacs.6b11412,10.1002/chem.201000420,10.1021/acs.orglett.6b01398,10.1002/adsc.20100071010.1002/ejic.202100870,10.1002/ejoc.202101112,10.1039/d1nj03706d,10.1021/acs.organomet.1c00324,10.1039/d1nj01698a,10.1016/j.jorganchem.2021.121754,10.1002/chem.202004132,10.1016/j.molstruc.2020.128635,10.1016/j.tet.2020.131493,10.1016/j.inoche.2020.107993,10.1021/acs.orglett.0c01127,10.1016/j.ica.2020.119457,10.1039/c9nj06438a,10.1021/acs.organomet.9b00672,10.1515/pac-2019-0220,10.1002/ejoc.201901189,10.3987/REV-19-914,10.1007/s10600-019-02705-8,10.1021/acs.joc.8b02904,10.1021/acs.organomet.8b00451,10.1016/j.mencom.2019.01.001,10.1016/j.arabjc.2015.06.012,10.1002/cctc.201702019,10.1002/cptc.201700232,10.1016/j.jorganchem.2018.01.044,10.6023/cjoc201708058,10.1002/ejoc.201700837,10.1246/cl.170466,10.1007/s12039-017-1338-7,10.1016/j.ccr.2017.03.007,10.3987/COM-16-S(S)21,10.1021/jacs.6b11412,10.1039/c6dt03944h,10.1007/s10562-016-1880-9,10.1021/acscatal.6b02269,10.1055/s-0035-1562788,10.1002/bkcs.10819,10.1021/acs.orglett.6b01398,10.1002/bkcs.10777,10.1515/znb-2016-0011,10.1007/3418_2015_127,10.1055/s-0034-1378867,10.1016/j.jorganchem.2015.04.019,10.1002/cctc.201403057,10.1016/j.jorganchem.2015.03.007,10.1016/j.ica.2014.11.005,10.6023/cjoc201411004,10.1016/j.molcata.2014.10.031,10.1021/cs5014927,10.1021/om5007177,10.1002/chem.201404618,10.1039/c5ra03522h,10.1016/j.tetlet.2014.11.020,10.1021/jo502260x,10.1002/ejoc.201402881,10.1021/om500593s,10.1021/om500484q,10.1002/ejoc.201402919,10.1016/j.tet.2014.07.059,10.1016/j.tetlet.2014.01.148,10.1021/jo501291y,10.1016/j.tet.2014.04.059,10.1002/ejoc.201402120,10.1016/j.tet.2014.02.051,10.1021/jo402799t,10.1016/j.tet.2013.11.056,10.1021/ol403209k,10.6023/cjoc201307035,10.1039/c4dt00461b,10.1039/c3ra45547e,10.1016/j.tet.2013.10.089,10.1016/j.tet.2013.10.043,10.1016/j.tetlet.2013.04.123,10.1021/ic302854t,10.1016/j.tet.2012.12.030,10.1002/cctc.201200417,10.1039/c3cs35521g,10.1039/c3ra23188g,10.1002/ejoc.201200918,10.1016/j.tet.2012.05.075,10.1021/jo301270t,10.1021/om300399j,10.1002/ejoc.201200444,10.1021/ol301221p,10.1021/om201101g,10.1021/jo202472k,10.1021/om200937d,10.1021/om201271y,10.1021/jo202577m,10.1002/ejic.201101036,10.1021/jo2022982,10.1039/c2gc16111g,10.1039/c2cc18150a,10.1002/ejoc.201101527,10.1021/om200864z,10.1021/jo202037x,10.1021/jo2015246,10.1016/j.tet.2011.07.048,10.1590/S0103-50532011000900018,10.1021/ol201469r,10.1002/adsc.201100151,10.1007/s12039-011-0092-5,10.1021/om200246k,10.1002/adsc.201100101,10.1016/j.tetlet.2010.11.133,10.1016/j.jorganchem.2011.01.003,10.1021/ol200128y,10.1002/chem.201003403,10.1002/ejoc.201001519,10.1021/cr100259t,10.1021/cr1002276,10.1002/adsc.201000710,10.1039/c1cc12240a,10.1002/chem.201002273,10.1039/c0dt01211d,10.1039/c1dt10928f,10.1016/j.bmcl.2010.07.130,10.1021/ol101592r,10.1016/S1872-2067(09)60089-9,10.1021/om100302g,10.1002/ejoc.201000134,10.1055/s-0030-1258116,10.1021/ol100720x,10.1002/ejoc.201000147,10.1002/ejoc.201000251,10.1016/j.tetlet.2009.10.096,10.1039/c0cc03107k,10.1002/chem.201000420,10.1039/c0dt00021c,10.1002/adsc.200900566,10.1021/ol9015892,10.1002/ejoc.200900581,10.1021/cr900074mKelly12/2/2021
107
84FALSEejoc.20100014710.1002/ejoc.201000147https://sci-hub.wf/10.1002/ejoc.201000147https://doi.org/10.1002/ejoc.201000147NiC-O ActivationElaineTRUE468312010Yang, LM
Ni-II-(sigma-Aryl) Complex Catalyzed Suzuki Reaction of Aryl Tosylates with Arylboronic Acids
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
A practical, efficient protocol was developed for the Suzuki reaction of aryl tosylates with arylboronic acids The process was promoted by a nickel-based catalyst system consisting of the easily available Ni-II-(sigma-aryl) complex and the simple ligand PPh3 in toluene in the presence of the base K2CO3, The convenient operation, high yield, generality, and low cost make this method viable for most common laboratories and applicable in large-scale preparations
Chinese Acad Sci5/1/2010Csp2_ar-Csp2_arE-NuOBOTsB(OH)2ArylArylK2CO3Ionic-CO3Weak0.36_10.1021/jo1024464,10.1002/adsc.201100151,10.1021/ol503061c,10.1039/c0cc03107k,10.1021/jo4005537,10.1021/jo3001194,10.1002/ejoc.201001519,10.1021/om300566m10.1002/chem.202004132,10.1002/aoc.5662,10.1021/acs.orglett.9b02858,10.1039/c8nj05503c,10.1016/j.tet.2018.10.025,10.1021/acs.organomet.7b00446,10.1038/s41570-017-0025,10.1002/ejic.201601351,10.1021/acs.joc.6b01619,10.1055/s-0035-1562343,10.1016/j.tetlet.2015.10.009,10.1016/j.jorganchem.2015.04.019,10.1002/cctc.201403057,10.1002/adsc.201400761,10.1021/ol503061c,10.1021/om5008743,10.1002/ejoc.201402919,10.1016/j.tet.2014.04.059,10.1021/om500156q,10.6023/cjoc201307035,10.1039/c4ra11520a,10.1002/aoc.3000,10.1016/j.tet.2013.04.073,10.1021/jo4005537,10.1021/jo3018878,10.1002/cctc.201200417,10.3390/molecules171012121,10.1021/om300566m,10.1021/jo301270t,10.1016/j.tet.2012.05.030,10.1021/jo3001194,10.1021/om201271y,10.1039/c1ob06404e,10.1002/anie.201207428,10.1016/j.poly.2011.05.009,10.1002/adsc.201100151,10.1016/j.jorganchem.2011.03.038,10.1002/adsc.201100101,10.1021/jo1024464,10.1002/ejoc.201001519,10.1021/cr100259t,10.1002/chem.201002273,10.1039/c0cc03107k12/16/2021
108
115FALSEacs.orglett.8b0102110.1021/acs.orglett.8b01021https://sci-hub.wf/10.1021/acs.orglett.8b01021https://doi.org/10.1021/acs.orglett.8b01021NiC-N ActivationGerryTRUE415892018Rueping, M
Cross-Coupling of Amides with Alkylboranes via Nickel-Catalyzed C-N Bond CleavageORG LETT
A protocol for the nickel-catalyzed alkylation of amides was established. The use of alkylboranes as nucleophilic partners allowed the use of mild reaction conditions and compatibility of various functional groups with respect to both coupling partners. The catalytic alkylation proceeded selectively at the amides in the presence of other functional groups as well as other carboxylic acid derived moieties.
Rhein Westfal TH Aachen
5/18/2018Csp2-Csp3E-NuNB
N(Me)Ph
9-BBN
Carbonyl
AlkylK2CO3Ionic-CO3_xxx10.1039/c8qo00764k,10.1021/acs.orglett.9b04497,10.1002/anie.202103327,10.1021/acscatal.0c00246,10.1002/anie.20200227110.1007/s11426-021-1035-5,10.1016/j.tetlet.2021.153147,10.1002/anie.202103327,10.1021/acs.joc.0c02868,10.1021/acs.joc.0c02843,10.1021/acs.joc.0c02209,10.1021/acs.orglett.0c03260,10.1039/d0cc04960c,10.1055/s-0040-1707301,10.1016/j.comptc.2020.112889,10.1039/d0dt01846e,10.1021/acs.joc.0c00160,10.1002/anie.202002271,10.1021/acscatal.0c01000,10.1021/acs.orglett.0c00442,10.1021/acscatal.0c00246,10.3390/catal10030296,10.1007/s11426-019-9665-5,10.1021/acs.orglett.9b04497,10.1021/acs.joc.9b02826,10.1002/adsc.201900819,10.1021/acs.orglett.9b02862,10.1021/acs.joc.9b01103,10.1002/adsc.201900485,10.1021/acs.joc.9b00208,10.1039/c9qo00106a,10.1021/acs.joc.9b00583,10.1021/acs.orglett.9b00233,10.1039/c8gc03726d,10.1002/asia.201801317,10.3390/catal9010053,10.1039/c8qo00764k,10.1002/adsc.201800879,10.1021/acs.orglett.8b02911,10.3390/molecules23102681,10.3390/molecules23102412,10.1021/acs.oprd.8b00182,10.1039/c8cc03954bLong1/5/2022
109
121FALSEejoc.20100151910.1002/ejoc.201001519https://sci-hub.wf/10.1002/ejoc.201001519https://doi.org/10.1002/ejoc.201001519NiC-O ActivationLongTRUE599312011Yang, LM
Room-Temperature Nickel-Catalysed Suzuki-Miyaura Reactions of Aryl Sulfonates/Halides with Arylboronic Acids
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Room-temperature Suzuki-Miyaura aryl-aryl cross-coupling reactions have been achieved in high yields by using an easily accessible, air-stable Ni-II-(sigma-aryl) complex as precatalyst without either the pretreatment of organometallic reagents or the presence of external reductants. The Ni-II complex, in conjunction with monophosphane ligands such as PCy3 center dot HBF4 or PPh3, allowed the efficient cross-coupling of aryl sulfonates (OTs, OMs) and/or halides (Cl, Br, I) with arylboronic acids at room temperature in toluene/water in the presence of K2CO3 as base.
Chinese Acad Sci3/1/2011Csp2_ar-Csp2_arE-NuOBOTsB(OH)2ArylArylK2CO3Ionic-CO3Weak0.36_10.1021/jo2022982,10.1021/ol403209k,10.1002/anie.201805611,10.1021/jacs.6b11412,10.1021/jo300547v,10.1021/jo3001194,10.1021/ol503061c,10.1021/ol401727y,10.1021/jo501291y10.1039/d0ra10248b,10.1002/aoc.6158,10.1002/chem.202004132,10.1039/d0ra04362a,10.1021/acs.orglett.0c01600,10.1002/aoc.5662,10.1002/slct.201903749,10.1021/acs.orglett.9b02858,10.1007/s11227-019-02896-5,10.1039/c8nj05503c,10.1039/c8nj04157a,10.1016/j.tet.2018.10.025,10.1021/acs.organomet.8b00589,10.1002/anie.201805611,10.1021/acscatal.8b00933,10.1002/chem.201801241,10.1039/c8qo00156a,10.1021/acs.orglett.8b00496,10.1039/c7cc06881f,10.1038/s41570-017-0025,10.1021/jacs.6b11412,10.1016/j.jorganchem.2016.09.018,10.1002/ajoc.201600319,10.1055/s-0035-1562342,10.1021/acs.organomet.6b00059,10.1002/anie.201505699,10.1002/adsc.201500461,10.1021/acs.orglett.5b00766,10.1021/jo502541t,10.1016/j.catcom.2014.08.037,10.1039/c4ra16452k,10.1016/j.tetlet.2014.11.020,10.1021/ol503061c,10.1002/ejoc.201402881,10.1007/s11426-014-5138-3,10.1021/jo501291y,10.1016/j.tet.2014.04.059,10.1021/om500156q,10.1021/cs4009946,10.1021/ol403209k,10.6023/cjoc201307035,10.1039/c4ra11520a,10.1021/ol401727y,10.1002/aoc.3000,10.1016/j.tet.2013.04.073,10.1021/ol401021x,10.1039/c3cs35521g,10.1021/jo301270t,10.1021/jo300547v,10.1021/jo3008258,10.1021/ol301221p,10.1021/jo3001194,10.1021/jo2022982,10.1039/c2ra21632aKelly12/15/2021
110
59FALSEejoc.20120044410.1002/ejoc.201200444https://sci-hub.wf/10.1002/ejoc.201200444https://doi.org/10.1002/ejoc.201200444NiC-O ActivationElaineTRUE368322012Han, FS
An Efficient Suzuki-Miyaura Coupling of Aryl Sulfamates and Boronic Acids Catalyzed by NiCl2(dppp)
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
The SuzukiMiyaura cross-coupling of aryl sulfamates and boronic acids was investigated by using [1,3-bis(diphenylphosphanyl)propane]nickel(II) chloride {NiCl2(dppp)} as the catalyst. The results showed that NiCl2(dppp) is a highly active and general catalyst that allows effective SuzukiMiyaura cross-coupling of aryl sulfamates with a slight excess amount of the boronic acid (1.2 equiv.) in the presence of a low catalyst loading (generally 1.01.5 mol-%). The method also displays broad generality not only to various aryl sulfamates, but also to an array of boronic acids. Furthermore, various functional groups are tolerated. These apparent advantages make NiCl2(dppp) a practical and reliable catalyst system for the SuzukiMiyaura coupling of aryl sulfamates.
Chinese Acad Sci5/29/2012Csp2_ar-Csp2_arE-NuOB
OSO2NMe2
B(OH)2ArylArylK3PO4Ionic-PO4Weak0.36TM10.1039/c4qo00321g,10.1002/adsc.201400460,10.1021/ol401727y,10.1021/om500452c,10.1021/jo4005537,10.1021/ol301847m,10.1021/jacs.7b04973,10.1021/jacs.6b1141210.1016/j.mcat.2020.110915,10.1002/aoc.5662,10.1021/acsomega.9b04450,10.1039/c9ob00313d,10.1016/j.tet.2018.10.025,10.1016/j.jorganchem.2018.01.019,10.1021/acs.organomet.7b00642,10.1021/jacs.7b04973,10.1039/c6qo00533k,10.1002/adsc.201601105,10.1038/s41570-017-0025,10.1021/jacs.6b11412,10.1016/j.jorganchem.2016.09.026,10.1021/acs.orglett.6b02330,10.1055/s-0035-1562342,10.1002/anie.201505699,10.1002/ejoc.201500987,10.1016/j.jorganchem.2015.01.009,10.1039/c4qo00321g,10.1039/c5ra12742d,10.1021/om500452c,10.1002/adsc.201400460,10.1002/chem.201404380,10.1002/ejoc.201402919,10.1021/om5001327,10.1021/jo500409r,10.1021/ja4118413,10.6023/cjoc201307035,10.1039/c3ob41382a,10.1021/ol402262c,10.1021/ol401727y,10.1002/aoc.3000,10.1021/jo4005537,10.1039/c3cs35521g,10.1021/ol301847m12/16/2021
111
56FALSEhlca.1980063042710.1002/hlca.19800630427https://sci-hub.wf/10.1002/hlca.19800630427https://doi.org/10.1002/hlca.19800630427NiC-O ActivationKelly16-FebTRUE363431980
CONSIGLIO, G
NICKEL-CATALYZED ASYMMETRIC ALKYLATION OF SOME CHIRAL AND ACHIRAL ALLYLIC ALCOHOLS
HELVETICA CHIMICA ACTA
SWISS FED INST TECHNOL,TECH CHEM LAB,CH-8092 ZURICH,SWITZERLAND.
6/6/1980Csp3-Csp3E-NuOMgOHMgXAllylAlkylNo baseNo BaseStrong-0.81_10.1016/S0040-4020(01)87621-3,10.1021/jo982312e,10.1039/c3983000011210.6023/cjoc202106021,10.1021/acscatal.1c03449,10.1021/acs.orglett.0c01109,10.1021/acs.orglett.9b03633,10.6023/cjoc201809037,10.1002/cjoc.201800237,10.1002/anie.201703380,10.1021/acs.chemrev.5b00162,10.1021/ja0730718,10.1021/jo982312e,10.1021/jo981130h,10.1016/S0040-4039(97)00178-0,10.1021/jo961615a,10.1021/ja00140a015,10.1080/00397919508015850,10.1021/om00018a016,10.1016/0022-328X(91)80189-Q,10.1021/cr00098a001,10.1021/cr00091a007,10.1039/dt9890000161,10.1021/jo00390a013,10.1016/0022-328X(87)87150-4,10.1016/S0040-4020(01)87621-3,10.1021/ja00293a038,10.1016/S0040-4039(00)98166-8,10.1039/c39830000112,10.1021/ic00131a090,10.1016/S0020-1693(00)86943-1,10.1016/S0022-328X(00)95293-8,10.1021/ja00397a048,10.1039/c39810000681checked by Kelly2/7/2022
112
211FALSE0022-328x(85)80354-510.1016/0022-328x(85)80354-5https://sci-hub.wf/10.1016/0022-328x(85)80354-5https://doi.org/10.1016/0022-328x(85)80354-5NiC-O ActivationLongTRUE1252641985Tsuji, J
REACTIONS OF ALLYLIC CARBONATES CATALYZED BY PALLADIUM, RHODIUM, RUTHENIUM, MOLYBDENUM, AND NICKEL-COMPLEXES - ALLYLATION OF CARBONUCLEOPHILES AND DECARBOXYLATION-DEHYDROGENATION
JOURNAL OF ORGANOMETALLIC CHEMISTRY
02/27/1985Csp3-Csp3E-NuOH
OCO2Me
HAlkylAlkylNo baseNo BaseMedium0.31_10.1021/ol702122d,10.1016/S0040-4039(97)10240-410.1021/jacs.1c05701,10.1021/acs.joc.9b01293,10.1002/anie.201902509,10.1055/s-0037-1611784,10.1021/acs.joc.8b03267,10.6023/cjoc201809037,10.1039/c8cy00613j,10.1021/acs.joc.8b00583,10.1080/10610278.2017.1288910,10.1002/chem.201603532,10.5059/yukigoseikyokaishi.74.885,10.1039/c6qo00192k,10.5059/yukigoseikyokaishi.74.45,10.1055/s-0034-1378720,10.1021/jo502078c,10.1002/chem.201402825,10.1016/j.tetlet.2013.08.032,10.1002/chem.201201267,10.1021/ol301248d,10.1002/ejoc.201200104,10.1016/j.ccr.2011.10.018,10.1002/chem.201103418,10.1007/3418_2011_15,10.1002/ejoc.201100350,10.1021/jo2007169,10.1016/j.jorganchem.2010.10.037,10.1021/cr1002744,10.1007/978-3-642-15334-1_7,10.1021/ol102106v,10.1007/s10562-010-0383-3,10.1016/j.tetlet.2009.05.079,10.5059/yukigoseikyokaishi.67.584,10.1016/j.tet.2008.11.007,10.1002/cssc.200800256,10.1055/s-2008-1078446,10.1351/pac200880050861,10.1021/ol702122d,10.1021/om0608004,10.1039/b614015g,10.1002/chem.200600173,10.1002/anie.200600100,10.2174/138527206775192979,10.1002/anie.200462513,10.1016/j.tetlet.2004.07.032,10.1073/pnas.0307271101,10.1002/chem.200305340,10.1016/j.tetasy.2003.08.044,10.1021/ja035983p,10.1016/S0040-4020(03)00866-4,10.1021/ol0343562,10.1055/s-2003-37120,10.2174/1385272023373545,10.1021/ar010068z,10.1021/ja011428g,10.1016/S0277-5387(01)00934-2,10.1016/S0040-4039(01)01467-8,10.1021/cr000666b,10.1016/S0040-4020(01)00351-9,10.5059/yukigoseikyokaishi.59.170,10.1021/ja005689m,10.1081/SCC-100104004,10.1021/ja003168t,10.1016/S0040-4039(00)01448-9,10.1021/ja0003831,10.1021/ja9929537,10.1021/om990533k,10.5059/yukigoseikyokaishi.57.608,10.1002/(SICI)1521-3773(19991102)38:21<3163::AID-ANIE3163>3.0.CO;2-#,10.1021/cr9403695,10.1021/ja981560p,10.1039/a802876a,10.1021/ja980030q,10.1021/jo971268k,10.1016/S0040-4039(97)10240-4,10.1021/om970514f,10.1021/cr9409804,10.1080/00397919608004631,10.1021/cr00036a007,10.1016/0040-4039(95)00286-3,10.1016/0022-328X(94)24751-4,10.5059/yukigoseikyokaishi.52.800,10.1016/0022-328X(94)88138-3,10.1007/BF00695820,10.1016/0022-328X(93)83025-Q,10.1016/0022-328X(93)80158-8,10.1021/om00028a069,10.1002/jhet.5570290509,10.1016/0022-328X(92)83346-J,10.1021/ja00033a033,10.1016/S0065-3055(08)60016-7,10.5059/yukigoseikyokaishi.49.919,10.1021/ja00182a018,10.1039/dt9900002407,10.1039/dt9900001645,10.1021/ja00163a060,10.1021/ja00202a068,10.1246/bcsj.62.2913,10.1016/0304-5102(89)85054-0,10.1016/0022-328X(89)87015-9,10.1016/0022-328X(89)85259-3,10.1021/cr00091a007,10.1016/S0040-4039(01)80770-X,10.1016/0022-328X(88)83167-X,10.1016/0022-328X(88)80540-0,10.1016/0022-328X(87)80052-9,10.1021/jo00390a007,10.1016/0022-328X(87)87149-8,10.1021/ar00136a003,10.1246/bcsj.60.1525,10.1021/jo00382a002,10.1016/0022-328X(87)80312-1,10.1016/S0040-4020(01)81672-0,10.1016/S0040-4020(01)87666-3,10.1039/c39860000922,10.1016/S0040-4020(01)90587-3,10.1016/S0040-4020(01)87277-X,10.1016/S0040-4039(00)84086-1,10.1016/S0040-4039(00)84380-4,10.1016/S0040-4039(00)85219-3Kelly2/10/2022
113
205FALSE0040-4039(80)80215-210.1016/0040-4039(80)80215-2https://sci-hub.wf/10.1016/0040-4039(80)80215-2https://doi.org/10.1016/0040-4039(80)80215-2NiC-O ActivationLong7-FebTRUE1145681980Kumada , M
NICKEL-CATALYZED CROSS-COUPLING OF SILYL ENOL ETHERS WITH GRIGNARD-REAGENTS - REGIO-CONTROLLED AND STEREOCONTROLLED SYNTHESIS OF OLEFINS
TETRAHEDRON LETTERS
07/9/1980Csp2-Csp3E-NuOMgOTMSMgXVinylAlkylNo baseNo BaseStrong-0.27_10.1016/S0040-4039(99)00439-6,10.1039/c4cc08187k,10.1021/ol4011757,10.1021/jo00199a030,10.1021/ol203322v10.1021/acs.orglett.1c03844,10.1021/acscatal.1c01077,10.1021/acs.orglett.0c02236,10.1021/acs.orglett.9b00946,10.1002/anie.201808509,10.1002/anie.201802434,10.1016/j.tetlet.2018.02.073,10.1246/cl.160712,10.1021/jacs.6b07844,10.1002/chem.201602150,10.1007/s41061-016-0043-1,10.1016/j.tet.2016.02.069,10.1016/bs.adomc.2016.07.001,10.1039/c6ob01765g,10.1021/acs.organomet.5b00561,10.1039/C5QO00243E,10.1039/c4cc08187k,10.1021/ol4011757,10.1021/jo4002382,10.1007/3418_2012_42,10.1039/c3ra44884c,10.1021/ol203322v,10.1002/anie.201203778,10.1246/cl.2011.1001,10.1021/cr100259t,10.1002/chem.201002273,10.1055/s-0029-1219165,10.1021/ja8079548,10.1002/anie.200903146,10.1055/s-2008-1067194,10.1002/anie.200701365,10.1107/S1600536806003643,10.1002/ejoc.200500279,10.1055/s-2004-834878,10.1016/j.tet.2004.03.072,10.1002/anie.200453859,10.1016/S0040-4039(03)01804-5,10.1021/jo026449n,10.1021/ol034141s,10.1021/ja0208456,10.1021/ja016838j,10.1039/b104340b,10.1021/jo991196s,10.1039/a906589j,10.1016/S0040-4039(99)00439-6,10.1021/jo980249n,10.1021/jo971636k,10.1021/om960799g,10.1016/S0040-4039(97)00187-1,10.1021/jo961900u,10.1002/chem.19960021006,10.1021/jo960617s,10.1016/0040-4020(96)00246-3,10.1021/jo00119a022,10.1039/c39950000717,10.1021/cr00032a009,10.1016/S0040-4039(00)73479-4,10.1016/S0040-4020(01)81896-2,10.1021/jo00070a022,10.1021/ja00068a092,10.3891/acta.chem.scand.47-0716,10.1016/S0040-4039(00)60454-9,10.1039/p19920003419,10.1002/cber.19911241222,10.1016/0040-4039(91)80851-V,10.1016/0304-5102(90)85256-H,10.1021/ja00185a051,10.1021/ja00225a037,10.1021/ar00146a001,10.1016/S0040-4020(01)85098-5,10.1016/S0040-4039(00)86039-6,10.1039/p19870002569,10.1016/0022-328X(87)87150-4,10.1021/jo00378a033,10.1246/cl.1987.2203,10.1016/S0040-4039(00)96684-X,10.1021/ja00279a068,10.1021/ja00271a037,10.1351/pac198658050767,10.1021/jo00206a036,10.1021/jo00220a042,10.1021/ja00300a031,10.1021/om00128a003,10.1246/bcsj.57.108,10.1021/jo00196a002,10.1021/jo00199a030,10.1021/ja00313a032,10.1021/ja00328a063,10.1021/ja00336a033,10.1139/v83-436,10.1016/S0040-4020(01)91955-6,10.1016/S0040-4039(00)88045-4,10.1016/S0040-4039(00)94166-2,10.1021/bk-1982-0185.ch007,10.1139/v82-098,10.1246/cl.1982.223,10.1246/cl.1982.1641,10.1016/S0022-328X(00)95293-8,10.1016/S0040-4039(01)90390-9Kelly1/4/2022
114
274FALSE0040-4039(96)01302-010.1016/0040-4039(96)01302-0https://sci-hub.wf/10.1016/0040-4039(96)01302-0https://doi.org/10.1016/0040-4039(96)01302-0NiC-O ActivationGerry14-MarTRUE492381996Mortreux, A
Bis(aminophosphine)-nickel complexes as efficient catalysts for alkylation of allylic acetates with stabilized nucleophiles
TETRAHEDRON LETTERS
The alkylation of a variety of allylic acetates with dimethyl malonate catalysed by nickel-diphosphine complexes is reported. It is shown that in most cases bis(aminophosphine) type ligands lead to much more efficient catalysts than dppb and other usual diphosphines. The use of chiral ligands during the alkylation of 3-acetoxycyclohexene affords dimethyl cyclohex-2-enylmalonate in up to 40% ee. Copyright (C) 1996 Published by Elsevier Science Ltd
8/19/1996Csp3-Csp3E-NuOHOAcHAllylAlkylNo baseNo BaseMedium0.31_10.1002/anie.201507494,10.1021/ol702122d10.1002/ejic.202100820,10.1055/a-1657-5543,10.1021/acscatal.1c03449,10.1016/j.tetlet.2021.152916,10.1002/adsc.202001338,10.1039/d0qo01087a,10.1021/acs.chemrev.9b00682,10.1021/acs.orglett.0c01109,10.1039/c9gc03619a,10.6023/cjoc201809037,10.1002/anie.201507494,10.1515/pac-2014-1108,10.1021/jo501886w,10.1016/j.jorganchem.2014.01.025,10.1016/j.ica.2012.01.057,10.1016/j.ica.2011.07.056,10.1007/978-3-642-15334-1_7,10.1002/aoc.1547,10.1021/om800460h,10.1135/cccc20080705,10.1021/ol702122d,10.1016/j.poly.2006.05.035,10.1016/j.ccr.2006.02.033,10.1002/chem.200501180,10.1080/104265090969225,10.1016/j.poly.2004.12.009,10.1021/jo049394t,10.1021/ar030239v,10.1080/02603590390464216,10.1021/cr020027w,10.1016/S1387-7003(02)00558-0,10.1016/S0022-328X(01)00764-1,10.1016/S0040-4039(00)01448-9,10.1002/(SICI)1521-3765(20000117)6:2<353::AID-CHEM353>3.0.CO;2-U,10.1039/a809488h,10.1016/S1381-1169(98)00067-3,10.1016/S0010-8545(98)00088-5,10.1021/ja981560p,10.1039/a802876a,10.1016/S0040-4020(97)10383-0,10.1016/S0040-4020(97)10208-3,10.1016/S0040-4039(96)02510-5,10.1016/S0040-4039(96)02329-53/14/2022
115
124FALSEc2dt30886j10.1039/c2dt30886jhttps://sci-hub.wf/10.1039/c2dt30886jhttps://doi.org/10.1039/c2dt30886jNiC-N ActivationShihongTRUE41552012Wang, ZX
Nickel complexes supported by quinoline-based ligands: synthesis, characterization and catalysis in the cross-coupling of arylzinc reagents and aryl chlorides or aryltrimethylammonium saltsDALTON T
Lithium and nickel complexes bearing quinoline-based ligands have been synthesized and characterized. Reaction of 8-azidoquinoline with Ph2PNHR (R = p-MeC6H4, Bu-t) affords N-(8-quinolyl)-iminophosphoranes RNHP(Ph-2)=N(8-C9H6N) (1a, R = p-MeC6H4; 1b, R = Bu-t. C9H6N = quinolyl)). Reaction of 1a with (DME)NiCl2 generates a nickel complex [NiCl2{N(8-C9H6N)=P(Ph-2)NH-(p-MeC6H4)}] (2a). Treatment of 1b with (DME)NiCl2 and following with NaH produces [NiCl{(1,2-C6H4)P(Ph)(NHBut)=N(8-C9H6N)}] (4). Complex 4 was also obtained by reaction of (DME)NiCl2 with [Li{(1,2-C6H4)P(Ph)(NHBut)=N(8-C9H6N)}] (5) prepared through lithiation of 1b. Reaction of 2-PyCH2P(Ph-2)=N(8-C9H6N) (6, Py = pyridyl) and PhN=C(Ph)CH2P(Ph-2)=N(8-C9H6N) (8), respectively, with (DME)NiCl2 yields two five-coordinate N,N,N-chelate nickel complexes, [NiCl2{2-PyCH2P(Ph-2)=N(8-C9H6N)}] (7) and [NiCl2{PhN=C(Ph)CH2P(Ph-2)=N(8-C9H6N)}] (9). Similar reaction between Ph2PCH2P(Ph-2)=N(8-C9H6N) (10) and (DME)NiCl2 results in five-coordinate N,N,P-chelate nickel complex [NiCl2{Ph2PCH2P(Ph-2)=N(8-C9H6N)}] (11). Treatment of [(8-C9H6N)N=P(Ph-2)](2)CH2 (12) [prepared from (Ph2P)(2)CH2 and 2 equiv. of 8-azidoquinoline] with LiBun and (DME) NiCl2 successively affords [NiCl{(8-C9H6N)NP(Ph-2)}(2)CH] (13). The new compounds were characterized by H-1, C-13 and P-31 NMR spectroscopy (for the diamagnetic compounds), IR spectroscopy (for the nickel complexes) and elemental analysis. Complexes 2a, 4, 7, 9, 11 and 13 were also characterized by single-crystal X-ray diffraction techniques. The nickel complexes were evaluated for the catalysis in the cross-coupling reactions of arylzinc reagents with aryl chlorides and aryltrimethylammonium salts. Complex 7 exhibits the highest activity among the complexes in catalyzing the reactions of arylzinc reagents with either aryl chlorides or aryltrimethylammonium bromides.
Univ Sci & Technol China
7/20/2012Csp2_ar-Csp2_arE-NuNZn
NMe3+Br-
ZnXArylArylNo baseNo BaseE-H_10.1016/j.tet.2017.06.004,10.1021/om500452c,10.1039/c3ob41989d,10.1002/anie.201511197,10.1039/c4qo00321g10.1016/j.tet.2021.132431,10.1021/acscatal.0c03341,10.1021/acs.organomet.9b00834,10.1021/acscatal.9b00218,10.1016/j.ica.2018.10.069,10.1002/ajoc.201800560,10.1134/S0022476618050207,10.1039/c8dt00828k,10.1002/asia.201701342,10.1002/ijch.201700044,10.1002/asia.201701132,10.1016/j.tet.2017.06.004,10.1039/c7qo00174f,10.1007/s11243-017-0122-3,10.1039/c6qo00670a,10.1007/s40010-016-0289-6,10.1021/acs.inorgchem.6b01162,10.1002/anie.201511197,10.1039/c5dt03721b,10.1039/c6cc04531f,10.1021/acs.joc.5b02557,10.1002/chem.201503596,10.1021/acs.orglett.5b02458,10.1002/ejic.201500693,10.1002/ejoc.201500987,10.1002/chem.201500192,10.1039/c4qo00321g,10.1039/c5dt01392e,10.1021/om500452c,10.1016/j.ica.2014.07.065,10.1080/00958972.2014.886109,10.1039/c4dt00927d,10.1039/c3ob41989d,10.1039/c4ob01041h,10.1016/j.tet.2013.09.039,10.1002/ejoc.201300850,10.1021/ol400971q,10.1021/ja308950dLong12/22/2021
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125FALSEc6sc00702c10.1039/c6sc00702chttps://sci-hub.wf/10.1039/c6sc00702chttps://doi.org/10.1039/c6sc00702cNiC-H ActivationGerry17-FebTRUE451452016Doyle, AG
Nickel-catalyzed enantioselective arylation of pyridineCHEM SCI
We report an enantioselective Ni-catalyzed cross coupling of arylzinc reagents with pyridinium ions formed in situ from pyridine and a chloroformate. This reaction provides enantioenriched 2-aryl-1,2-dihydropyridine products that can be elaborated to numerous piperidine derivatives with little or no loss in ee. This method is notable for its use of pyridine, a feedstock chemical, to build a versatile, chiral heterocycle in a single synthetic step.
Princeton Univ3/8/2016TRUETRUEFALSECsp2_ar-Csp2_arNu-NuHHHHHetArylNo baseNo BaseNu-H_xx10.1021/jacs.7b0238910.1021/jacs.1c11092,10.1021/acscatal.1c05780,10.1038/s41467-022-27989-3,10.1021/jacs.1c11092,10.1016/j.tet.2021.132316,10.1039/d1sc03860e,10.1055/a-1577-7638,10.1021/acscatal.1c01544,10.6023/A21040131,10.1038/s41467-021-22374-y,10.1021/acs.orglett.1c00352,10.1021/acscatal.0c04474,10.1021/acs.orglett.0c02828,10.1021/acscatal.0c01491,10.1002/ajoc.202000337,10.1021/jacs.0c04486,10.1021/acs.joc.0c00314,10.3390/molecules25030563,10.1021/acscatal.9b03874,10.1021/acs.orglett.9b03503,10.1021/acscatal.9b03367,10.1021/acs.joc.9b01865,10.1016/j.tetlet.2019.151041,10.1021/jacs.9b02013,10.1002/anie.201813716,10.1038/s41557-018-0178-5,10.1021/acs.orglett.8b03576,10.3390/catal8120632,10.1021/acs.joc.8b01601,10.1039/c8qo00689j,10.1021/acs.joc.8b01232,10.1002/ajoc.201800285,10.1021/acs.joc.8b00928,10.1021/jacs.8b02568,10.1021/jacs.7b12212,10.1002/anie.201709163,10.1021/acs.orglett.7b01664,10.1021/acs.joc.7b00560,10.1002/adsc.201601065,10.1021/jacs.7b02389,10.1021/acs.orglett.6b03824,10.1021/acscatal.6b01962,10.1021/acscatal.6b0169311/15/20212016FALSEFALSEFALSEFALSE774105
117
170FALSE0040-4039(96)01984-310.1016/0040-4039(96)01984-3https://sci-hub.wf/10.1016/0040-4039(96)01984-3https://doi.org/10.1016/0040-4039(96)01984-3NiC-O ActivationGerryTRUE881281996Kobayashi, Y
Nickel-catalyzed coupling reaction of lithium organoborates and aryl mesylates possessing an electron withdrawing group
TETRAHEDRON LETTERS
In the presence of NiCl2(PPh(3))(2) as catalyst, p-methoxycarbonylpheny mesylate (5) and tosylate (6) react with lithium arylborates 4 (Ar = 2-furyl; Ph, p-Me-Ph, p-MeO-Ph) at room temperature to afford the coupling products in high yields. Similarly. mesylates 9-11 coupled with these berates 4 efficiently. Copyright (C) 1996 Elsevier Science Ltd
TOKYO INST TECHNOL,DEPT BIOMOL ENGN,MIDORI KU,4259 NAGATSUTA CHO,YOKOHAMA,KANAGAWA 226,JAPAN.
11/18/1996Csp2_ar-Csp2_arE-NuOBOTsB(nep)ArylArylNo baseNo BaseWeak0.36_10.1016/j.tetlet.2006.01.145,10.1021/ja038752r,10.1002/ejoc.201001519,10.1002/ejoc.200900067,10.1002/adsc.201100151,10.1021/jo2022982,10.1021/ol016526l,10.1016/S0022-328X(02)01174-9,10.1002/anie.201101461,10.1021/acscatal.9b00744,10.1016/S0040-4020(98)00809-6,10.1246/cl.2005.79610.1039/d0cs00688b,10.1021/acs.orglett.9b02236,10.1021/acscatal.9b00744,10.1021/acs.orglett.8b03560,10.1039/c8cc07781a,10.1002/anie.201706868,10.1021/acs.chemrev.6b00772,10.1038/s41570-017-0025,10.1021/acscatal.6b02927,10.1021/acscatal.6b02964,10.1055/s-0035-1562343,10.1007/3418_2015_129,10.1021/acs.orglett.5b01283,10.1002/aoc.3289,10.1021/ja5070763,10.6023/cjoc201307035,10.1016/j.tet.2012.12.030,10.1039/c3ra44195d,10.1039/c3cs35521g,10.1021/jo300290v,10.1021/jo2022982,10.1039/c2dt12187e,10.1002/adsc.201100151,10.1016/j.tetlet.2010.11.133,10.1002/ejoc.201001519,10.1021/cr100259t,10.1021/cr1002276,10.1016/j.tetlet.2010.10.163,10.1002/anie.201101461,10.1002/chem.201002273,10.1055/s-0030-1258116,10.1016/j.tetlet.2010.03.110,10.1016/j.tetlet.2009.10.096,10.1021/om900771v,10.1002/ejoc.200900067,10.1021/ol802493z,10.1021/ol802049t,10.1021/ja805810p,10.1021/jo8014819,10.1021/ja804672m,10.1021/ja711449e,10.1002/anie.200802157,10.1002/anie.200803193,10.1021/jo7019064,10.1002/ejoc.200600469,10.1016/j.tetlet.2006.07.085,10.1021/cc0600066,10.1016/j.tetlet.2006.01.145,10.1016/j.tetlet.2006.01.020,10.1021/jo051394l,10.1246/cl.2005.796,10.1246/cl.2004.1322,10.1021/cr020101a,10.1021/ja038752r,10.1021/om034187p,10.1021/ja036947t,10.1021/ja035835z,10.1021/jo026449n,10.1021/cc020045r,10.1021/jo020640f,10.1016/S0040-4020(02)01188-2,10.1021/ja027190t,10.1016/S0022-328X(02)01264-0,10.1016/S0022-328X(02)01174-9,10.1016/S0040-4039(02)00718-9,10.1246/bcsj.75.137,10.1021/ol016526l,10.1021/jm000290u,10.1016/S0040-4020(00)00814-0,10.1016/S0040-4020(00)00815-2,10.1021/jo991337q,10.5059/yukigoseikyokaishi.57.845,10.1016/S0040-4039(99)00239-7,10.1016/S0040-4020(98)00809-6,10.1016/S0040-4020(97)10206-X,10.1016/S0040-4020(97)10233-2,10.1016/S0010-8545(97)00067-2Kelly1/14/2022
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101FALSEj.tet.2006.03.12310.1016/j.tet.2006.03.123https://sci-hub.wf/10.1016/j.tet.2006.03.123https://doi.org/10.1016/j.tet.2006.03.123NiC-O ActivationKellyTRUE524972006Knochel, P
An efficient Negishi cross-coupling reaction catalyzed by nickel(II) and diethyl phosphiteTETRAHEDRON
A combination of diethyl phosphite-DMAP and Ni(II) salts forms a very effective catalytic system for the cross-coupling reactions of arylzinc halides with aryl, heteroaryl, and alkenyl bromides. chlorides. triflates. and nonaflates. The choice of solvent is quite important and the mixture of THF-N-ethylpyrrolidinone (NEP) (8: 1) was found to be optimal. The reaction usually requires only 0.05 moll % of NiCl2 or Ni(acac)(2) as catalyst and proceeds at room temperature within 1-48 h. (c) 2006 Elsevier Ltd. All rights reserved.
Univ Munich8/7/2006Csp2_ar-Csp2_arE-NuOZnONfZnXArylArylNo baseNo BaseWeak0.53_x10.1021/ol702499h,10.1002/anie.201100683,10.1021/om500452c,10.1039/c2dt30886j10.1021/acs.inorgchem.1c01720,10.1021/acscatal.1c01077,10.1021/acs.chemrev.9b00682,10.1021/acs.orglett.8b03417,10.1002/adsc.201800596,10.1002/anie.201805396,10.1016/j.apcata.2018.04.031,10.1002/ajoc.201700324,10.1002/anie.201605744,10.1021/acs.joc.6b00002,10.1021/jacs.5b11889,10.1039/c5nj03450g,10.1039/c5ob02364e,10.1055/s-0035-1560640,10.1055/s-0034-1380141,10.1016/j.tetlet.2014.11.118,10.1039/c4dt02158d,10.1021/om500452c,10.1039/c4ob01041h,10.1039/c3ob41382a,10.1055/s-0032-1316904,10.1002/adsc.201200369,10.1002/ejic.201101036,10.1039/c2dt30886j,10.1021/jo201840n,10.1021/jo201630e,10.1002/chem.201101037,10.1002/adsc.201100165,10.3762/bjoc.7.147,10.1021/jo200904g,10.1021/jo102417x,10.1021/cr100259t,10.1021/jo1018969,10.1002/anie.201100683,10.1039/c0cc03064c,10.1002/ijch.201000033,10.1021/om9006399,10.1002/adsc.200900566,10.1039/b805648j,10.1134/S1070428009010011,10.1055/s-0028-1087347,10.1021/jo8018686,10.1021/jo801445y,10.1055/s-2008-1067095,10.1002/anie.200703382,10.1039/b810973g,10.1002/asia.200700391,10.1021/ol702499h,10.1021/ol701927g,10.1016/j.jorganchem.2007.01.021Kelly2/7/2022
119
128FALSEc5cy01299f10.1039/c5cy01299fhttps://sci-hub.wf/10.1039/c5cy01299fhttps://doi.org/10.1039/c5cy01299fNiC-H ActivationWilliam8-FebFALSE432332015Balaraman, E#N/ANickel-catalyzed direct alkynylation of C(sp(2))-H bonds of amides: an inverse Sonogashira strategy to ortho-alkynylbenzoic acids
CATAL SCI TECHNOL
Nickel-catalyzed direct alkynylation of C(sp(2))-H bonds of amides using commercially available, inexpensive 8-aminoquinoline as a removable bidentate directing group is described. The present ortho-alkynylation has a broad substrate scope, functional group tolerance and high regiocontrol, and can be scaled up. The efficiency and selectivity of this strategy provide sustainable routes to a diverse array of ortho-alkynylbenzoic acids under Ni-(II)-catalyzed conditions.
CSIR NCL10/23/2015y_x10.1021/acscatal.6b01120,10.1039/c6qo00149a10.1039/d1cc05263b,10.1002/adsc.202100992,10.1002/chem.202100093,10.1039/d0cs00447b,10.1016/j.tetlet.2021.152825,10.1002/chem.202002888,10.1039/d0sc01084g,10.1002/cjoc.201900468,10.1021/acs.chemrev.9b00495,10.2174/1385272824999200616114037,10.1021/jacs.9b10868,10.1016/j.trechm.2019.06.002,10.1016/j.tetlet.2019.06.003,10.1039/c9cy00009g,10.1021/acs.organomet.8b00899,10.1039/c8sc05063e,10.1021/acs.orglett.9b00351,10.1038/s42004-019-0132-5,10.1021/acs.chemrev.8b00507,10.1039/c8cs00201k,10.1039/c8cc03445a,10.1021/acs.organomet.8b00177,10.1002/asia.201800102,10.1021/acscatal.8b01116,10.1039/c8ob00585k,10.1021/acs.joc.8b00174,10.1039/c7cc05532c,10.1021/acs.orglett.7b02247,10.1021/jacs.7b03548,10.1002/chem.201605657,10.1002/cssc.201700321,10.1002/chem.201700587,10.1002/chem.201605306,10.1021/acs.orglett.6b02549,10.1007/s41061-016-0053-z,10.1021/acscatal.6b01120,10.1002/adsc.201600080,10.1021/acs.joc.6b00129,10.1021/acs.orglett.6b00175,10.1021/acs.orglett.6b00095,10.1039/c6gc01728b,10.1039/c6qo00149a#N/A
120
129FALSEacscatal.7b0144410.1021/acscatal.7b01444https://sci-hub.wf/10.1021/acscatal.7b01444https://doi.org/10.1021/acscatal.7b01444NiC-N ActivationGerryTRUE643542017Garg, NK
Kinetic Modeling of the Nickel-Catalyzed Esterification of AmidesACS CATAL
Nickel-catalyzed coupling reactions provide exciting tools in chemical synthesis. However, most methodologies in this area require high catalyst loadings, which commonly range from 10-20 mol % nickel. Through an academic-industrial collaboration, we demonstrate that kinetic modeling can be used strategically to overcome this problem, specifically within the context of the Ni-catalyzed conversion of amides to esters. The successful application of this methodology to a multigram-scale coupling, using only 0.4 mol % Ni, highlights the impact of this endeavor.
Univ Calif Los Angeles
7/1/2017TRUETRUEFALSEyCsp2-Osp2E-NuNH
N(Me)Ph
H
Carbonyl
ORNo baseNo Base_10.1021/jacs.7b06191,10.1002/anie.201808560,10.1021/acscatal.7b0368810.1021/acscatal.1c05738,10.1039/d1ob02349g,10.1002/ejoc.202100645,10.1002/ejoc.202100478,10.1177/1747519820987530,10.1039/d0ra09639c,10.1021/acs.orglett.0c03260,10.1007/s11426-020-9883-3,10.1016/j.tetlet.2020.152444,10.1021/acscatal.0c03334,10.1016/j.trechm.2020.08.001,10.1021/acs.orglett.0c02457,10.1007/s41981-020-00090-w,10.1002/aoc.5626,10.1021/acscatal.9b05074,10.1021/acs.orglett.0c00885,10.1007/s10562-019-02966-6,10.1007/s11426-019-9665-5,10.1021/acs.joc.9b02826,10.1021/acs.orglett.9b03434,10.1007/3418_2020_44,10.1021/acssuschemeng.9b04667,10.1039/c9cc05763c,10.1021/acs.joc.9b01103,10.1021/acs.orglett.9b02513,10.1021/acs.oprd.9b00170,10.1002/ejoc.201900531,10.1039/c9qo00106a,10.1016/j.tetlet.2019.04.004,10.1021/acs.jchemed.8b00489,10.3390/molecules24071234,10.1021/acs.orglett.8b03476,10.1021/acs.organomet.8b00589,10.1039/c8qo00591e,10.3390/molecules23102681,10.1002/anie.201808560,10.1039/c8gc00500a,10.1016/j.tetlet.2018.01.097,10.1002/chem.201800336,10.1021/acs.orglett.8b00080,10.1021/acscatal.7b03688,10.1021/acscatal.7b02599,10.1070/RCR4795,10.1021/jacs.7b06191Long11/2/2021JUL2017FALSEFALSEFALSEFALSE774381
121
130FALSEc5sc01589h10.1039/c5sc01589hhttps://sci-hub.wf/10.1039/c5sc01589hhttps://doi.org/10.1039/c5sc01589hNiC-H ActivationGerryTRUE431#N/A2015Nolan, SP
Synthesis of (diarylmethyl)amines using Ni-catalyzed arylation of C(sp(3))-H bondsCHEM SCI
The first nickel catalyzed deprotonative cross coupling between C(sp(3))-H bonds and aryl chlorides is reported, allowing the challenging arylation of benzylimines in the absence of directing group or stoichiometric metal activation. This methodology represents a convenient access to the (diarylmethyl)amine moiety, which is widespread in pharmaceutically relevant compounds.
Univ St Andrews6/12/2015TRUETRUEFALSEyCsp3-Csp2_arE-NuXHClHAlkylArylNo baseNo Base_xx10.1039/c5sc03704b10.1002/tcr.202100113,10.1021/acs.orglett.1c00835,10.1021/acsomega.1c01116,10.1016/j.trechm.2020.06.001,10.1016/j.chempr.2020.04.005,10.1055/s-0039-1690731,10.1002/ajoc.201900554,10.1021/acs.orglett.9b02550,10.1002/tcr.201800093,10.3390/inorganics7060078,10.1021/acscatal.9b00777,10.1016/j.tet.2019.03.033,10.1021/acs.orglett.8b03394,10.1039/c8sc02965b,10.1021/acsomega.8b02324,10.1039/c8cc06408c,10.1039/c8ob02000k,10.1021/acs.chemrev.8b00349,10.1021/acs.orglett.8b02536,10.1021/acs.orglett.8b02331,10.1039/c8qo00421h,10.1002/adsc.201800396,10.1002/anie.201802492,10.1021/acs.joc.8b00491,10.1073/pnas.1718474115,10.1021/acs.orglett.7b03262,10.1055/s-0036-1588514,10.1039/c7dt01912b,10.1021/acs.orglett.7b01886,10.1039/c6qo00846a,10.1021/acs.orglett.7b01471,10.1002/cssc.201700321,10.1002/adsc.201601105,10.1021/acs.organomet.6b00769,10.1039/c6cc09654a,10.1002/chem.201604739,10.1021/acscatal.6b02392,10.1021/jacs.6b05288,10.1002/adsc.201600654,10.1007/s41061-016-0053-z,10.1002/adsc.201600075,10.1039/c5sc03704b,10.1021/acs.orglett.5b0289811/15/20212015FALSEFALSEFALSEFALSE684973
122
155FALSEj.tet.2012.04.00510.1016/j.tet.2012.04.005https://sci-hub.wf/10.1016/j.tet.2012.04.005https://doi.org/10.1016/j.tet.2012.04.005NiC-O ActivationShihongTRUE7817892012Chatani, N
Ni(0)/NHC-catalyzed amination of N-heteroaryl methyl ethers through the cleavage of carbon-oxygen bondsTETRAHEDRON
Ni(0)/NHC-based catalyst system can promote the amination of N-heteroaryl methyl ethers via the cleavage of normally unreactive carbon oxygen bonds. Electron-deficient N-heteroarenes including pyridine, quinoline, isoquinoline, and quinoxaline undergo amination to afford aminopyridine and related heteroarenes, which constitute an important class of compounds. (C)2012 Elsevier Ltd. All rights reserved.
Osaka Univ7/1/2012TRUEFALSEFALSECsp2_ar-Nsp3E-NuOHOMeHAryl
Morpholine
NaOtBuIonic-OtBuStrong-0.28_shihong added10.1021/ol403209k,10.1021/acs.orglett.5b02200,10.1002/anie.201607646,10.1002/anie.201511486,10.1002/ejic.201900692,10.1002/anie.201410875,10.1002/anie.201510497,10.1021/ol503707m,10.1002/chem.201603436,10.1021/jacs.7b04973,10.1002/anie.201806790,10.1021/acs.orglett.7b00556,10.1021/acscatal.8b03436,10.1021/ol502583h,10.1021/jacs.9b02751,10.1021/acscatal.8b01879,10.1246/cl.15093610.1515/pac-2021-0110,10.1039/d1qo00549a,10.1021/acs.chemrev.0c00088,10.1039/d0nj01610a,10.1002/cjoc.201900506,10.1246/cl.200083,10.1246/cl.200099,10.1055/s-0039-1690010,10.1002/chem.201904288,10.1002/ejic.201900692,10.1021/acs.orglett.9b01805,10.1055/s-0037-1611732,10.1021/jacs.9b02751,10.1007/3418_2018_19,10.1021/acscatal.8b03436,10.1002/anie.201806790,10.1021/acscatal.8b01879,10.1016/j.jorganchem.2018.01.019,10.1039/c8ob00911b,10.1038/s41467-018-03928-z,10.1021/acs.organomet.8b00046,10.1021/acs.orglett.8b00674,10.1021/acs.orglett.8b00060,10.1039/c7cc08709h,10.1002/chem.201703266,10.1055/s-0036-1589093,10.1055/s-0036-1590962,10.1021/jacs.7b04973,10.1248/cpb.c17-00487,10.1021/acs.orglett.7b01549,10.1002/ejoc.201700660,10.1002/anie.201610203,10.1021/acs.joc.6b02701,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1016/j.cclet.2016.11.002,10.1246/bcsj.20160391,10.1016/j.jorganchem.2016.12.029,10.1002/anie.201610409,10.1021/jacs.6b10998,10.1021/acscatal.6b03040,10.1021/acscatal.6b02964,10.1002/anie.201607646,10.1002/ajoc.201600411,10.1246/cl.160712,10.1002/chem.201603436,10.1002/tcr.201500305,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1002/anie.201510497,10.1002/anie.201511486,10.1021/acscatal.5b02021,10.1016/bs.adomc.2016.07.001,10.1246/cl.150936,10.1002/chem.201502114,10.1021/acs.orglett.5b02200,10.1021/acs.orglett.5b01229,10.1021/acs.joc.5b01005,10.1016/j.tet.2015.02.088,10.1021/jacs.5b03955,10.1021/acs.accounts.5b00051,10.1002/ejoc.201500226,10.1002/anie.201410875,10.1016/j.ejmech.2014.12.020,10.1016/j.ica.2015.01.005,10.1021/ol503707m,10.1016/j.molcata.2014.10.031,10.1039/c5qo00039d,10.1021/ol502583h,10.1039/c4ob01088d,10.1038/nature13274,10.1021/ol403209k,10.1039/c3ob42053a,10.1039/c4cs00206g,10.1016/j.tca.2013.07.013,10.1007/3418_2012_42Kelly12/1/2021
123
68FALSEj.tet.2013.04.09610.1016/j.tet.2013.04.096https://sci-hub.wf/10.1016/j.tet.2013.04.096https://doi.org/10.1016/j.tet.2013.04.096NiC-O ActivationLongTRUE391172013Kalyani, D
Nickel-catalyzed intramolecular C-H arylation using aryl pivalates as electrophilesTETRAHEDRON
This paper describes a method for nickel catalyzed intramolecular C-H arylation using aryl pivalates as electrophiles. The transformation is efficient for the synthesis of diverse electronically and sterically differentiated dibenzofurans. Additionally, the method could be expanded toward the synthesis of carbazoles. Preliminary mechanistic studies of the transformation are also described. (C) 2013 Elsevier Ltd. All rights reserved.
St Olaf Coll7/8/2013Csp2_ar-Csp2_arE-NuOHOPivHArylArylCs2CO3Ionic-CO3Medium0.33_xxx10.1021/jacs.7b0497310.1055/a-1349-3543,10.1021/acs.chemrev.0c00088,10.1021/acscatal.0c02990,10.1021/acs.chemrev.9b00682,10.1002/cjoc.201900506,10.1021/acs.joc.9b02094,10.1021/acs.orglett.9b01593,10.1055/s-0037-1609636,10.1021/acs.chemrev.8b00507,10.1007/3418_2018_19,10.3390/catal9010076,10.1016/j.tet.2018.10.025,10.1002/adsc.201800729,10.1002/ajoc.201800207,10.1016/j.jorganchem.2018.01.019,10.1039/c7dt04560c,10.1021/jacs.7b04973,10.1021/acs.orglett.7b01938,10.1021/acs.joc.7b00550,10.1016/j.tet.2017.02.021,10.1246/bcsj.20160365,10.1002/anie.201610409,10.1021/acscatal.6b02964,10.1007/s41061-016-0043-1,10.1007/s41061-016-0053-z,10.1002/adsc.201500822,10.1039/c6ra07130a,10.1016/j.tet.2015.08.023,10.1002/anie.201503204,10.1016/j.tetlet.2015.03.039,10.1007/s10562-014-1449-4,10.1055/s-0034-1378555,10.1016/j.jfluchem.2014.02.008,10.1515/pac-2014-5033,10.1021/ol403304t1/6/2022
124
133FALSEanie.20170908710.1002/anie.201709087https://sci-hub.wf/10.1002/anie.201709087https://doi.org/10.1002/anie.201709087NiC-H ActivationGerry8-FebTRUE46132017
Ackermann, L
Bifurcated Nickel-Catalyzed Functionalizations: Heteroarene C-H Activation with Allenes
ANGEW CHEM INT EDIT
A unified strategy for nickel(0)-catalyzed C-H allylations, alkenylations, and dienylations has been realized through versatile hydroarylations of allenes with ample scope. Thus, an inexpensive nickel catalyst modified with a N-heterocyclic carbene ligand enabled the direct transformation of C-H bonds of biologically relevant imidazole and purine derivatives with full control of regio- and chemoselectivity.
Georg August Univ Gottingen
12/11/2017TRUEFALSEFALSEaddition?yCsp2_ar-Csp2Nu-NuHHHHHetVinylNo baseNo BaseNu-H_xx10.1039/d1sc06097j,10.1021/acscatal.1c04743,10.1021/acs.orglett.1c02346,10.1021/acs.orglett.1c02219,10.1021/acs.orglett.1c01521,10.1002/tcr.202100113,10.1055/a-1471-7307,10.1039/d1qo00309g,10.1039/d0qo01127d,10.1021/acs.chemrev.0c00803,10.1039/d0ob02008g,10.1021/acs.orglett.0c03077,10.1002/ejoc.202001333,10.3390/molecules25214970,10.1016/j.xcrp.2020.100178,10.1021/acs.orglett.0c02609,10.1002/anie.202003216,10.1021/jacs.0c04837,10.1039/d0cy00965b,10.1039/d0cs00149j,10.1021/acs.chemrev.9b00634,10.1039/c9cc09076b,10.1021/jacs.9b08342,10.1002/anie.201904774,10.1016/j.cclet.2019.04.027,10.1002/anie.201904214,10.1021/acs.organomet.9b00060,10.3390/inorganics7060078,10.1021/acs.orglett.9b00958,10.1021/acs.orglett.9b01139,10.1002/cjoc.201800568,10.1039/c9cy00009g,10.1039/c8sc05063e,10.1021/acs.chemrev.8b00507,10.1002/anie.201813191,10.1039/c8cc09165j,10.1002/chem.201805441,10.1039/c8cy01860j,10.1002/slct.201802644,10.1021/acscatal.8b03066,10.1021/acscatal.8b01720,10.1002/ajoc.201800133,10.1002/anie.201801324,10.1039/c8sc01741g12/29/2021DEC 112017FALSEFALSEFALSEFALSE565015891
125
134FALSEc7cc07457c10.1039/c7cc07457chttps://sci-hub.wf/10.1039/c7cc07457chttps://doi.org/10.1039/c7cc07457cNiC-N ActivationGerryTRUE453#N/A2017Huang, PQ
Ni-Catalyzed cross-coupling reactions of N-acylpyrrole-type amides with organoboron reagents
CHEM COMMUN
The catalytic conversion of amides to ketones is highly desirable yet challenging in organic synthesis. We herein report the first Ni/bisNHC-catalyzed cross-coupling of N-acylpyrrole-type amides with arylboronic esters to obtain diarylketones. This method is facilitated by a new chelating bis-NHC ligand. The reaction tolerates diverse functional groups on both arylamide and arylboronic ester partners including sensitive ester and ketone groups.
Xiamen Univ12/4/2017Csp2-Csp2_arE-NuNB
N-pyrrolyl
B(nep)
Carbonyl
ArylK3PO4Ionic-PO4_x10.1021/acs.orglett.8b01021,10.1021/acs.orglett.9b00242,10.1021/acscatal.7b0368810.1039/d1dt02849a,10.1038/s42004-021-00575-2,10.1016/j.jorganchem.2021.122042,10.1002/chem.202004840,10.1021/acs.orglett.0c03260,10.1002/adsc.202000794,10.1021/acscatal.0c03334,10.1039/d0qo00797h,10.1002/ejoc.202000575,10.1021/acs.joc.0c00790,10.6023/cjoc202001028,10.1038/s41467-020-16948-5,10.1002/ajoc.202000139,10.1021/acs.orglett.0c00885,10.1021/acs.orglett.0c00485,10.1002/ejoc.201901730,10.1007/s11426-019-9665-5,10.1039/c9ob02421b,10.1021/acs.orglett.9b03434,10.1002/adsc.201900819,10.1055/s-0039-1690002,10.1021/acs.joc.9b01699,10.1039/c9sc02035g,10.1002/adsc.201900485,10.1039/c9nj01748h,10.1016/j.tet.2018.12.024,10.1021/acs.orglett.9b00242,10.1002/tcr.201800079,10.1021/acs.joc.8b02567,10.1016/j.tetlet.2018.08.035,10.1021/acs.oprd.8b00182,10.1039/c8cc03954b,10.1021/acs.orglett.8b01579,10.1021/acscatal.8b01380,10.1002/ejoc.201800175,10.1039/c8ob00907d,10.1021/acs.orglett.8b01021,10.6023/A18020054,10.1021/acs.orglett.8b00949,10.1021/acs.joc.7b03068,10.1016/j.tetlet.2018.01.097,10.1039/c7qo01031a,10.1039/c7gc03534a,10.1021/acscatal.7b03688Long1/5/2022
126
114FALSEj.tetlet.2006.01.14510.1016/j.tetlet.2006.01.145https://sci-hub.wf/10.1016/j.tetlet.2006.01.145https://doi.org/10.1016/j.tetlet.2006.01.145NiC-O ActivationShihongTRUE5511262006Hu, QS
Ferrocenylmethylphosphines as ligands for room temperature Ni(0)-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl arenesulfonates and aryl chlorides
TETRAHEDRON LETTERS
Readily available ferrocenylmethylpliosphine was found as an efficient ligand for room temperature Ni(0)-catalyzed Suzuki-Miyaura cross-couplings of aryl arenesulfonates. Ferrocenylphosphine and its polymeric form were also found as useful ligands for Ni(0)-catalyzed Suzuki-Miyaura couplings of deactivated aryl chlorides. (c) 2006 Elsevier Ltd. All rights reserved.
CUNY Coll Staten Isl
4/3/2006Csp2_ar-Csp2_arE-NuOBOTsB(OH)2ArylArylK3PO4Ionic-PO4Weak0.36TM10.1039/b609064h,10.1002/ejoc.201000147,10.1021/jo7022558,10.1002/ejoc.201001519,10.1021/jo2022982,10.1021/ol101592r,10.1021/om300566m,10.1021/jo2000034,10.1021/jo070912k,10.1021/jo202037x,10.1021/ja903091g10.1002/slct.201903749,10.1021/acs.orglett.9b02858,10.1016/j.tet.2018.10.025,10.1021/acs.organomet.7b00446,10.1002/ejic.201601351,10.1002/adsc.201600205,10.6023/cjoc201408028,10.1002/ejoc.201402881,10.6023/cjoc201307035,10.3184/174751913X13726940260318,10.1002/cctc.201200417,10.1039/c3cs35521g,10.1021/om300566m,10.1021/jo301270t,10.1021/jo2022982,10.3987/COM-11-S(P)20,10.1002/anie.201207428,10.1021/jo202037x,10.5012/bkcs.2011.32.8.2584,10.1007/s12039-011-0092-5,10.1016/j.poly.2011.01.020,10.1016/j.jorganchem.2011.01.003,10.1021/jo2000034,10.1021/ol200128y,10.1002/ejoc.201001519,10.1021/cr100259t,10.1016/j.tetlet.2010.10.163,10.1002/chem.201002273,10.1039/c0nj00898b,10.1021/ol101592r,10.1021/jo100643j,10.1055/s-0030-1258116,10.1002/ejoc.201000147,10.1016/j.tetlet.2009.10.096,10.1021/ja903091g,10.1021/jo900098a,10.1021/ol802493z,10.1021/ja805810p,10.1021/jo8014819,10.1021/jo7022558,10.1039/b801888j,10.1016/j.tetlet.2007.08.089,10.1021/jo070912k,10.1016/j.ccr.2007.03.020,10.1246/cl.2007.928,10.1002/ejic.200601051,10.1021/ja070321b,10.1016/j.tetlet.2007.01.175,10.1039/b609064hKelly12/29/2021
127
136FALSEc8sc05445b10.1039/c8sc05445bhttps://sci-hub.wf/10.1039/c8sc05445bhttps://doi.org/10.1039/c8sc05445bNiC-H ActivationElaineTRUE541#N/A2019Lalic, G
Nickel-catalyzed anti-Markovnikov hydroarylation of alkenesCHEM SCI
We have developed a nickel-catalyzed hydroarylation of alkenes using aryl halides as coupling partners. Excellent anti-Markovnikov selectivity is achieved with aryl-substituted alkenes and enol ethers. We also show that hydroarylation occurs with alkyl substituted alkenes to yield linear products. Preliminary examination of the reaction mechanism suggests irreversible hydrometallation as the selectivity determining step of the hydroarylation.
Univ Washington3/21/2019TRUETRUEFALSEYCsp2_ar-Csp2E-NuXHIHArylVinylNaOtBuIonic-OtBu_Addition?10.1039/d1sc05605k,10.1021/acscatal.1c05441,10.1002/cjoc.202100763,10.1021/acscatal.1c04766,10.1021/acs.orglett.1c04073,10.1002/anie.202112390,10.1016/j.chempr.2021.10.015,10.1002/chem.202102847,10.1021/jacs.1c07851,10.1039/d1sc03121j,10.1021/acscatal.1c02299,10.1021/jacs.1c03228,10.1055/a-1523-3228,10.1021/acscatal.1c00908,10.1021/acs.organomet.0c00819,10.1002/anie.202016268,10.1002/ejoc.202100005,10.1002/qua.26621,10.1038/s41467-020-20888-5,10.1021/acscatal.0c05449,10.1002/anie.202012614,10.1021/acs.orglett.0c03542,10.1021/jacs.0c10333,10.1021/acscatal.0c03884,10.1002/anie.202011841,10.1038/s41467-020-19717-6,10.1021/acs.orglett.0c02923,10.1002/anie.202010840,10.1007/s11426-020-9838-x,10.1002/anie.202010386,10.1021/acs.joc.0c01509,10.1002/anie.202009195,10.1039/d0qo00428f,10.1021/acscatal.0c02115,10.1002/anie.202004414,10.1021/acsomega.0c00951,10.1021/acs.accounts.0c00032,10.1002/anie.202001742,10.1021/jacs.9b09415,10.1021/acs.orglett.9b03721,10.1002/anie.201912629,10.1021/acs.orglett.9b02577,10.1016/j.trechm.2019.05.007,10.1002/ejoc.201900940,10.1002/anie.201907045,10.1002/anie.20190718512/16/2021MAR 212019FALSEFALSEFALSEFALSE10113231
128
58FALSEs0022-328x(00)00164-910.1016/s0022-328x(00)00164-9https://sci-hub.wf/10.1016/s0022-328x(00)00164-9https://doi.org/10.1016/s0022-328x(00)00164-9NiC-O ActivationKelly16-FebTRUE383102000Deng, MZ
Nickel-catalyzed allylation of lithium 1-alkynyl(trialkoxy)borates with 1,3-disubstituted allyl carbonates
JOURNAL OF ORGANOMETALLIC CHEMISTRY
The first Suzuki-type cross-coupling of alkynylborates with 1,3-disubstitued allyl carbonates was studies. It was found that nickel complexes readily catalyzed the reaction giving normal coupling products in good to excellent yields. The nickel complexes of dppe or dppen revealed a higher catalytic activity than that of NiCl2(PPh3)(2) or NiCl2(dppf). This is a substrate-controlled reaction with high regioselectivity. The asymmetric cross-coupling reaction of alkynylborates with allyl carbonate enantioselectively produced an allyl substituted alkyne with 13%ee. (C) 2000 Elsevier Science S.A. All rights reserved.
Acad Sinica5/29/2000Csp3-Csp1E-NuOB
OCO2Et
B(OMe)3-Li+
AllylAlkyneNo baseNo BaseMedium0.31_x10.1021/ja300031w,10.1002/chem.201502329,10.1021/ol501672410.6023/cjoc202106021,10.1039/d1ob00465d,10.1021/acs.orglett.0c00108,10.1021/acs.orglett.9b03633,10.1002/adsc.201801527,10.6023/cjoc201809037,10.1002/slct.201702278,10.1039/c5cc10518h,10.1002/chem.201502329,10.1021/ol5016724,10.1021/ja406025p,10.1002/adsc.201200704,10.1016/j.jorganchem.2012.05.027,10.1055/s-0031-1290656,10.1021/ja300031w,10.1021/ol203154j,10.1002/ejoc.201101527,10.1021/cr1002276,10.1002/anie.201103581,10.1016/j.tetlet.2010.08.051,10.1055/s-0029-1218756,10.1021/ja905082c,10.1002/ejoc.200900104,10.1002/adsc.200800082,10.1021/ja800103z,10.1002/anie.200605113,10.1039/b803172j,10.1039/b502026c,10.1016/j.tetlet.2004.09.114,10.1021/ol048563t,10.1055/s-2004-832819,10.1016/j.tetlet.2004.05.033,10.1016/S0020-1693(02)01571-2,10.1016/S0010-8545(02)00122-41/25/2022
129
138FALSEc2cc32396f10.1039/c2cc32396fhttps://sci-hub.wf/10.1039/c2cc32396fhttps://doi.org/10.1039/c2cc32396fNiC-H ActivationGerryTRUE441#N/A2012Qu, GR
Nickel catalyzed alkylation of N-aromatic heterocycles with Grignard reagents through direct C-H bond functionalization
CHEM COMMUN
A novel protocol for nickel-catalyzed direct sp(2) C-H bond alkylation of N-aromatic heterocycles has been developed. This new reaction proceeded efficiently at room temperature using a Grignard reagent as the coupling partner. This approach provides new access to a variety of alkylated N-aromatic heterocycles which are potentially of great importance in medicinal chemistry.
Henan Normal Univ5/9/2012yCsp3-Csp2_arNu-NuMgHMgXHAlkylHetNo baseNo BaseNu-M_x10.1021/acscatal.6b0080110.1080/10406638.2020.1852287,10.1002/aoc.5869,10.1002/asia.202000277,10.1016/j.chempr.2020.04.005,10.1002/anie.201806631,10.1021/acs.chemrev.8b00507,10.1002/ejoc.201801684,10.1039/c8ob02476f,10.1021/acs.organomet.8b00025,10.1021/acs.joc.7b02269,10.1002/chem.201605657,10.1039/c6ob02330d,10.1021/acs.orglett.6b03287,10.1007/s41061-016-0053-z,10.1021/acscatal.6b00801,10.1021/acs.joc.6b00406,10.1021/jacs.6b02405,10.1039/c6ob00596a,10.1016/bs.aihch.2016.04.005,10.1016/j.jorganchem.2015.03.023,10.1002/anie.201504735,10.1021/acs.orglett.5b00878,10.1038/srep09139,10.1039/c5ra04406e,10.3998/ark.5550190.p008.915,10.1039/c4ob02488e,10.1039/c4cc09844g,10.1016/j.molcata.2014.05.013,10.1021/ol502314p,10.6023/cjoc201401024,10.1007/s10562-013-1170-8,10.1021/ol4033336,10.1039/c3gc41658e,10.1039/c3cc48069k,10.1021/jo402248d,10.1021/ja409803x,10.1517/13543776.2013.800857,10.1016/j.tet.2013.05.135,10.1002/chem.201203413,10.1055/s-0032-1317329,10.1039/c2cc35758e12/28/2021
130
139FALSEs0040-4039(99)00439-610.1016/s0040-4039(99)00439-6https://sci-hub.wf/10.1016/s0040-4039(99)00439-6https://doi.org/10.1016/s0040-4039(99)00439-6NiDeletedWilliam12-FebFALSE461271999Busacca, CA#N/ACross coupling of vinyl triflates and alkyl Grignard reagents catalyzed by Nickel(0)-complexes
TETRAHEDRON LETT
The scope and limitations of the Nickel(0)-catalyzed cross coupling of vinyl triflates with alkyl Grignard reagents have been studied. The effect of triflate substitution, solvent, and especially ligands have been examined. Ligands which are successful for sp(2) and sp Grignard reagents fail for sp(3) Grignard reagents. (C) 1999 Elsevier Science Lid. All rights reserved.
Boehringer Ingelheim Pharmaceut Inc
4/16/1999_10.1021/jo010452+10.1021/acs.orglett.1c00923,10.1021/acs.orglett.0c01683,10.1002/anie.201804479,10.1016/j.tetlet.2017.09.036,10.1002/adsc.201500928,10.1002/adsc.201500304,10.1021/acs.joc.5b00647,10.1002/jhet.1898,10.1007/s11426-013-5024-4,10.1016/j.tet.2013.11.102,10.1021/jo4002382,10.1039/c2dt31753b,10.1016/j.tet.2011.05.020,10.1134/S1560090411030031,10.1021/cr100327p,10.1039/c0cc05186a,10.1134/S1070427210050253,10.3906/kim-0906-69,10.1055/s-0029-1217964,10.1002/ejoc.200900487,10.3390/molecules14062032,10.1016/j.tetlet.2009.02.064,10.1002/ejic.200601051,10.1002/adsc.200505409,10.1002/ejoc.200500279,10.1055/s-2005-864790,10.1021/jo048300c,10.1002/ejoc.2004002636,10.1016/j.molcata.2004.03.029,10.1021/jo0498866,10.2174/0929867033456738,10.1021/jo026702j,10.1002/anie.200351817,10.1016/S0040-4039(02)01600-3,10.1021/jo010786z,10.1016/S0010-8545(01)00401-5,10.1021/jo010452+,10.1021/ol005956t,10.1021/ja0002058,10.1021/ja991703n#N/A
131
98FALSEs0022-328x(00)98073-210.1016/s0022-328x(00)98073-2https://sci-hub.wf/10.1016/s0022-328x(00)98073-2https://doi.org/10.1016/s0022-328x(00)98073-2NiC-O ActivationLong7-FebTRUE51451977
Swierczewski, G
REACTION OF ORGANOMAGNESIUM COMPOUNDS WITH ALLYL ALCOHOLS IN PRESENCE OF NICKEL-COMPLEXES
JOURNAL OF ORGANOMETALLIC CHEMISTRY
07/8/1977Csp3-Csp3E-NuOMgOHMgXAllylAlkylNo baseNo BaseStrong-0.81_10.1039/c39940001789,10.1002/hlca.19800630427,10.1002/chem.201502329,10.1021/ja00502a07410.3390/catal11050645,10.1021/acs.joc.0c00530,10.1021/acs.joc.0c00008,10.1002/cjoc.201800237,10.1002/chem.201502329,10.1038/nature13274,10.1002/asia.201000875,10.1139/V05-085,10.1021/jo981130h,10.1016/S0020-1693(97)05770-8,10.1021/jo9714674,10.1021/jo960458c,10.1246/bcsj.69.1065,10.1039/c39940001789,10.1016/S0957-4166(00)82091-1,10.1016/S0065-3055(08)60016-7,10.1021/jo00018a016,10.1021/ja00016a037,10.1021/jo00259a029,10.1021/jo00258a047,10.1002/cber.19881211108,10.1016/0022-328X(88)80540-0,10.1016/0040-4039(88)85165-7,10.1016/0022-328X(87)80053-0,10.1016/S0040-4039(00)98166-8,10.1246/cl.1984.1505,10.1016/S0040-4039(01)80135-0,10.1016/0022-328X(83)85087-6,10.1021/om00072a023,10.1021/ja00397a048,10.1021/ja00413a014,10.1016/S0040-4039(01)90263-1,10.1016/S0040-4039(01)82007-4,10.1002/hlca.19800630427,10.1016/S0022-328X(00)93827-0,10.5059/yukigoseikyokaishi.38.923,10.1016/0040-4020(80)80203-1,10.1016/S0022-328X(00)83205-2,10.1021/ja00502a074,10.1016/S0022-328X(00)92308-8,10.1016/S0022-328X(00)82039-2,10.1016/S0022-328X(00)91443-8,10.1016/S0022-328X(00)84071-1,10.1021/ja00488a030,10.1039/oc9777400175,10.1016/S0022-328X(00)93274-1Kelly1/19/2022
132
62FALSEs0022-328x(02)01174-910.1016/s0022-328x(02)01174-9https://sci-hub.wf/10.1016/s0022-328x(02)01174-9https://doi.org/10.1016/s0022-328x(02)01174-9NiC-O ActivationGerryTRUE37282002Kobayashi, Y
Scope and limitation of the nickel-catalyzed coupling reaction between lithium borates and mesylates
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Coupling reaction of aryl borates and mesylates derived from phenols and enols was studied. Mesylates with an electron-withdrawing group or ring were highly reactive at room temperature in the presence of NiCl2(PPh3)(2) to furnish the coupling products in good yields. (C) 2002 Elsevier Science B.V. All rights reserved.
Tokyo Inst Technol
7/1/2002Csp2_ar-Csp2_arE-NuOBOTsB(nep)ArylArylNo baseNo BaseWeak0.36_10.1021/ol101592r,10.1002/ejoc.20090006710.1021/acs.joc.9b02105,10.1016/j.tet.2019.130561,10.1021/acs.joc.9b01432,10.1515/pteridines-2018-0002,10.1080/00304948.2018.1405334,10.1038/s41570-017-0025,10.1021/acs.organomet.6b00059,10.1021/acs.joc.5b02830,10.6023/cjoc201307035,10.1039/c3cs35521g,10.1002/aoc.2852,10.1021/ja2077813,10.1021/ol200128y,10.1021/cr100259t,10.1021/cr1002276,10.1021/ol101592r,10.1021/ja103973a,10.1016/j.jorganchem.2009.02.019,10.1002/ejoc.200900067,10.3987/COM-08-S(F)69,10.1002/chem.200901432,10.1002/anie.200704162,10.1016/j.tet.2007.10.081,10.1055/s-2007-983845,10.1002/aoc.1270,10.1021/jo0623890,10.1055/s-2006-948173,10.1021/cc0600066,10.1002/adsc.200404191,10.1016/j.molcata.2004.05.008,10.1016/j.tet.2004.05.018,10.1016/j.ccr.2004.05.002,10.1039/b401077a,10.1021/om034115y1/14/2022
133
169FALSEs0040-4020(01)87621-310.1016/s0040-4020(01)87621-3https://sci-hub.wf/10.1016/s0040-4020(01)87621-3https://doi.org/10.1016/s0040-4020(01)87621-3NiC-O ActivationLong16-FebTRUE877431986
CONSIGLIO, G
ASYMMETRIC NICKEL-CATALYZED CROSS-COUPLING REACTION OF ALLYLIC SUBSTRATES WITH GRIGNARD-REAGENTSTETRAHEDRON
SWISS FED INST TECHNOL,DEPT IND & ENGN CHEM,UNIV STR 6,CH-8092 ZURICH,SWITZERLAND.
9/3/1985Csp3-Csp3-ring(s)E-NuOMgOPhMgXAlkylBenzylNo baseNo BaseStrong-0.32_10.1016/0040-4039(96)01302-0,10.1021/ol5016724,10.1039/c39950001863,10.1039/b002547j,10.1021/ja00132a039,10.1002/anie.201507494,10.1002/chem.20150232910.1002/ejic.202100820,10.6023/cjoc202106021,10.1002/anie.202102233,10.1039/c9cc09899b,10.1021/jacs.9b08734,10.6023/cjoc201809037,10.1002/cjoc.201800237,10.1002/anie.201703380,10.1002/anie.201507494,10.1002/chem.201502329,10.1021/acs.chemrev.5b00162,10.1021/ol5016724,10.1002/chem.201202251,10.1002/adsc.200900790,10.1016/j.jorganchem.2009.06.024,10.1039/b907722g,10.1002/chem.200801879,10.1021/jo800155a,10.1039/b809140d,10.1021/ol0713842,10.1021/ja0730718,10.1246/bcsj.79.1248,10.1139/V05-085,10.1021/ja0469030,10.1073/pnas.0307271101,10.1016/j.tetlet.2004.02.094,10.1016/S0040-4020(03)01234-1,10.1002/chem.200204657,10.1016/S0010-8545(02)00201-1,10.1021/jo010668b,10.1021/om010608w,10.1016/S0040-4039(00)00934-5,10.1039/a908076g,10.1002/(SICI)1521-3765(20000117)6:2<353::AID-CHEM353>3.0.CO;2-U,10.1039/b002547j,10.1021/jo982178y,10.1021/jo981745e,10.1016/S0020-1693(97)06085-4,10.1021/ja980222l,10.1246/bcsj.71.973,10.1016/S0020-1693(97)05770-8,10.1016/S0040-4020(97)10208-3,10.1016/S0040-4020(97)10212-5,10.1021/jo9714674,10.1246/bcsj.70.1943,10.1016/S1381-1169(97)00008-3,10.1021/ja970885n,10.1016/S0040-4039(97)00178-0,10.1016/S0040-4039(96)02510-5,10.1021/om960750a,10.1016/0022-328X(96)06251-1,10.1016/0040-4039(96)01302-0,10.1021/jo960458c,10.1246/bcsj.69.1065,10.1021/cr9409804,10.1039/c39950001863,10.1021/ja00132a039,10.1080/00397919508015850,10.1021/om00018a016,10.1016/0304-5102(93)85091-7,10.1016/0022-328X(92)80047-2,10.1016/0304-5102(92)80265-I,10.1021/ja00037a006,10.1016/0022-328X(91)80189-Q,10.1021/om00056a007,10.1021/jo00002a039,10.1021/ja00182a018,10.1021/om00162a014,10.1016/0304-5102(90)85186-L,10.1016/0304-5102(90)85092-V,10.1016/0022-328X(89)87301-2,10.1016/0304-5102(89)85054-0,10.1021/cr00091a007,10.1016/S0040-4020(01)89159-6,10.1021/cr00089a003,10.1021/ja00226a067,10.1016/0022-328X(88)80176-1,10.5059/yukigoseikyokaishi.46.356,10.1016/0022-328X(87)80053-0,10.1021/cr00080a005Kelly2/17/2022
134
79FALSEs0040-4020(97)10211-310.1016/s0040-4020(97)10211-3https://sci-hub.wf/10.1016/s0040-4020(97)10211-3https://doi.org/10.1016/s0040-4020(97)10211-3NiC-O ActivationGerryTRUE441871998Lautens, M
Scope of the nickel catalyzed asymmetric reductive ring opening reaction. Synthesis of enantiomerically enriched cyclohexenols.TETRAHEDRON
Subjecting a variety of oxabicyclo[2.2.1]heptenes to diisobutylaluminum hydride (DIBAL-H) in the presence of a catalytic amount of Ni(COD)(Z) and (R)-BINAP results in a highly enantioselective ring opening to generate cyclohexenols with ee's typically greater than 90%. The scope of this reaction has been delineated and alternative nickel catalysts have been examined which are less sensitive than NI(COD)(2). (C) 1998 Elsevier Science Ltd. All rights reserved.
Univ Toronto2/12/1998Csp3-Csp3E-NuOH
O(Ring-Opening)
HAlkylAlkylNo baseNo BaseWeak1_10.1021/jo982312e10.1021/acs.organomet.1c00017,10.1039/d0cs00702a,10.2174/1570179417666210105121115,10.1021/acs.chemrev.9b00682,10.1002/ejoc.202000672,10.1002/chem.201904053,10.1021/acs.orglett.9b00059,10.1021/acscatal.8b04787,10.2174/1570179416666181122094643,10.1002/ajoc.201800569,10.1039/c7qo01163f,10.1002/ejoc.201800503,10.1016/j.tetlet.2017.12.073,10.1039/c7ob00175d,10.1021/acs.orglett.6b02300,10.3390/molecules201219748,10.1021/acs.joc.5b00065,10.1021/jo500821m,10.1039/c3ob41560k,10.1002/ajoc.201300077,10.1007/3418_2012_38,10.1002/chem.201200257,10.1002/adsc.201000236,10.1021/jo100391e,10.1021/ol900834c,10.1021/op8000178,10.1016/j.jorganchem.2004.11.023,10.1016/j.tetlet.2004.12.067,10.1021/ol034251z,10.1021/ar010112a,10.1021/jo025822o,10.1039/b207344g,10.1021/ol0069204,10.1016/S0010-8545(99)00172-1,10.1021/ol005729r,10.1021/ja000134c,10.1021/ja993427i,10.1016/S0040-4020(99)00456-1,10.1021/jo982312echecked by Kelly1/25/2022
135
152FALSEs0040-4020(98)00809-610.1016/s0040-4020(98)00809-6https://sci-hub.wf/10.1016/s0040-4020(98)00809-6https://doi.org/10.1016/s0040-4020(98)00809-6NiC-O ActivationGerryTRUE789791998Miyaura, N
Synthesis of biaryls via nickel-catalyzed cross-coupling reaction of arylboronic acids and aryl mesylatesTETRAHEDRON
The cross-coupling reaction of arylboronic acids (1.3 equivs) with aryl methane-sulfonates was carried out in the presence of a nickel(0) catalyst (3 mol%) and K3PO4. nH(2)O (3 equivs). The use of toluene or the solvent and the nickel(0)-dppf catalyst prepared fram NiCl2(dppf) plus dppf with BuLi were recognized to be the most efficient to achieve both high yields and high selectivity. The reaction can be applied to various electron-deficient and -rich aryl methanesulfonates to give high yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
Hokkaido Univ10/22/1998Csp2_ar-Csp2_arE-NuOBOMsB(OH)2ArylArylK3PO4Ionic-PO4Weak0.36TMxxx10.1002/adsc.201100151,10.1016/S0022-328X(02)01174-9,10.1002/anie.201101461,10.1021/ol101592r,10.1002/ejoc.200900067,10.1021/jo1024464,10.1021/jo7022558,10.1021/jo010452+,10.1021/jo200003410.1021/acs.inorgchem.1c02157,10.1039/d0py01507e,10.1038/s41428-019-0259-3,10.6023/cjoc201804027,10.1021/acs.macromol.8b01333,10.1016/j.ccr.2017.03.007,10.1021/acscatal.6b02964,10.1021/acs.organomet.6b00723,10.1002/anie.201501908,10.1021/acs.orglett.5b01283,10.1016/j.tetlet.2014.11.020,10.1007/s11426-014-5138-3,10.1016/j.poly.2013.09.041,10.6023/cjoc201307035,10.14233/ajchem.2014.15478,10.14233/ajchem.2013.15232,10.1002/aoc.3000,10.1016/j.bmc.2013.01.067,10.1039/c3ra44195d,10.1039/c3cs35521g,10.1016/j.tet.2012.05.101,10.1021/om201271y,10.1002/adsc.201100151,10.1016/j.tetlet.2010.11.133,10.1021/jo2000034,10.1021/jo1024464,10.1021/ol200128y,10.1021/cr100259t,10.1021/cr1002276,10.1002/anie.201101461,10.1002/chem.201002273,10.1021/ol101592r,10.1055/s-0029-1218837,10.1055/s-0030-1258116,10.1016/j.tetlet.2009.10.096,10.1021/om900771v,10.1055/s-0029-1218283,10.1002/ejoc.200900067,10.1021/ol802493z,10.1021/om800711g,10.1021/ol802049t,10.1021/jo8014819,10.1021/ja711449e,10.1021/jo7022558,10.1002/anie.200802157,10.1002/anie.200803193,10.1016/j.tet.2007.10.007,10.1016/j.tetlet.2007.08.089,10.1016/j.tet.2007.05.064,10.1002/aoc.1270,10.1002/adsc.200700002,10.1002/ejoe.200600600,10.1021/cc0600066,10.1055/s-2005-918479,10.1055/s-2005-864790,10.1016/j.jorganchem.2004.12.022,10.1002/adsc.200404187,10.2174/0929867033456738,10.1002/ejoc.200300356,10.1021/cc020045r,10.1016/S0040-4020(02)00576-8,10.1016/S0022-328X(02)01174-9,10.1246/bcsj.75.137,10.1021/jo010452+,10.1016/S0040-4020(00)00814-0,10.1016/S0040-4020(00)00815-2,10.1016/S0010-8545(99)00172-1,10.1021/jo991337q,10.1071/CH99073Kelly1/3/2022
136
51FALSEs0040-4039(00)94062-010.1016/s0040-4039(00)94062-0https://sci-hub.wf/10.1016/s0040-4039(00)94062-0https://doi.org/10.1016/s0040-4039(00)94062-0NiC-O ActivationKelly16-FebTRUE333191983
CLAESSON, A
SYNTHESIS OF CONJUGATED DIENES BY NICKEL-CATALYZED REACTIONS OF 1,3-ALKADIEN-2-YL PHOSPHATES WITH GRIGNARD-REAGENTS
TETRAHEDRON LETTERS
UNIV UPPSALA,CTR BIOMED,DEPT ORGAN PHARMACEUT CHEM,S-75123 UPPSALA,SWEDEN.
9/15/1983Csp2-Csp3E-NuOMg
OP(O)(OEt)2
MgXVinylAlkylNo baseNo BaseStrong0.04_x10.1016/S0040-4039(99)00439-6,10.1021/jo010452+,10.1021/acscatal.7b0403010.1016/S0040-4039(00)94062-0checked by Kelly1/3/2022
137
147FALSEacs.organomet.6b0052910.1021/acs.organomet.6b00529https://sci-hub.wf/10.1021/acs.organomet.6b00529https://doi.org/10.1021/acs.organomet.6b00529NiC-H ActivationGerryTRUE482282017Shi, ZJ
Nickel-Catalyzed Oxidative Coupling of Unactivated C(sp(3))-H Bonds in Aliphatic Amides with Terminal Alkynes
ORGANOMETALLICS
In this work, we demonstrated Ni-catalyzed oxidative coupling of unactivated C(sp(3))-H bonds with terminal alkynes for construction of C(sp(3))-C(sp) bonds to synthesize alkyl-substituted internal alkynes. Different amides exhibited good compatibility. Preliminary mechanistic studies were conducted to account for this alkynylation.
Peking Univ1/9/2017Cu involvedyCsp3-Csp1Nu-NuHHHHAlkylAlkyneCs2CO3Ionic-CO3Nu-H_xx10.1021/jacs.7b04973,10.1002/anie.20201103610.1021/acs.chemrev.1c00519,10.1039/d1cc04802c,10.1002/adsc.202100992,10.1021/acscatal.1c03314,10.1016/j.tetlet.2021.153148,10.1021/acscatal.1c01417,10.1021/acs.organomet.1c00265,10.1002/anie.202100641,10.1021/acs.orglett.0c04137,10.1002/anie.202010784,10.1002/cssc.202001165,10.1055/s-0037-1610756,10.1021/acs.organomet.0c00021,10.1002/cjoc.202000204,10.1080/00397911.2020.1761392,10.1021/acscatal.0c01189,10.1002/cjoc.201900468,10.1002/slct.201904651,10.1021/acs.chemrev.9b00495,10.1016/j.tetlet.2019.151338,10.1016/j.tetlet.2019.151230,10.1038/s42004-019-0219-z,10.1016/j.trechm.2019.06.002,10.1002/adsc.201900532,10.1039/c9cc02347j,10.1002/cctc.201900254,10.1039/c9cy00009g,10.1039/c8sc05063e,10.1021/acs.joc.8b02738,10.1021/acs.chemrev.8b00507,10.1039/c8qo01215f,10.1039/c8qo01105b,10.1002/adsc.201801022,10.1021/jacs.8b07708,10.1039/c8cs00201k,10.1021/acs.organomet.8b00177,10.1055/s-0037-1609445,10.1002/asia.201800102,10.1002/cjoc.201700633,10.1002/adsc.201700798,10.6023/cjoc201703036,10.1039/c7cc04252c,10.1021/acs.orglett.7b00709,10.1021/acs.orglett.7b00479,10.1002/anie.201610426,10.1021/acs.organomet.6b0093812/29/2021
138
148FALSEjacs.9b0522410.1021/jacs.9b05224https://sci-hub.wf/10.1021/jacs.9b05224https://doi.org/10.1021/jacs.9b05224NiC-N ActivationLongTRUE9302019Shu, XZ
Reductive Coupling between C-N and C-O Electrophiles
J AM CHEM SOC
The cross-electrophile reaction is a promising strategy for C-C bond formation. Recent studies have focused mainly on reactions with organic halides. Here we report a coupling reaction between C-N and C-O electrophiles that demonstrates the possibility of constructing a C-C bond via C-N and C-O cleavage. Several reactions between benzyl/aryl ammonium salts and vinyl/aryl C-O electrophiles have been studied. Preliminary mechanistic studies revealed that the benzyl ammoniums were activated through a radical mechanism.
Lanzhou Univ8/14/2019TRUETRUEFALSECsp2-Csp3-ring(s)E-ENO
NMe3+OTf-
OAcVinylBenzylNaOAcIonic-ORE-H_10.1002/anie.202114556,10.1021/jacs.0c12462,10.1021/jacs.0c1309310.1002/anie.202200215,10.1021/acs.orglett.2c00207,10.1021/acs.oprd.1c00410,10.1055/s-0041-1737762,10.1021/acs.oprd.1c00410,10.1021/acscatal.1c04533,10.1021/acs.orglett.1c04018,10.1016/j.jpowsour.2021.230945,10.1002/anie.202114556,10.1021/acs.orglett.1c03590,10.1002/anie.202112876,10.1039/d1ob01690c,10.1039/d1ob01468d,10.6023/cjoc202103022,10.1021/jacs.1c05670,10.1021/acs.joc.1c01339,10.1039/d1ob00636c,10.1039/d1gc01907d,10.1039/d1qo00759a,10.1055/a-1467-2432,10.1021/jacs.1c00142,10.1055/a-1406-0484,10.1039/d0sc06586b,10.1021/jacs.0c13093,10.1021/acs.joc.0c02992,10.1021/jacs.0c12462,10.2174/1570179418666210224124931,10.1055/s-0040-1707342,10.1002/anie.202010737,10.7536/PC200607,10.1021/acscatal.0c03341,10.1021/acscatal.0c03903,10.1002/adsc.202000821,10.1021/jacs.0c07492,10.1038/s41467-020-18593-4,10.1021/acs.joc.0c01274,10.1039/d0cc02919j,10.1021/jacs.0c05730,10.1038/s41467-020-17224-2,10.1021/acs.orglett.0c01683,10.1246/cl.200216,10.1021/acs.orglett.0c01284,10.1021/acs.joc.0c00491,10.1039/d0qo00173b,10.1055/s-0039-1691525,10.1002/chem.202000412,10.1016/j.tetlet.2020.151647,10.1016/j.chempr.2019.12.026,10.1039/c9ob02667cLong11/1/2021AUG 142019FALSEFALSEFALSEFALSE1413212481
139
180FALSEs0040-4039(01)82980-410.1016/s0040-4039(01)82980-4https://sci-hub.wf/10.1016/s0040-4039(01)82980-4https://doi.org/10.1016/s0040-4039(01)82980-4NiC-O ActivationLongTRUE939681981Kumada , M
NICKEL-CATALYZED CROSS-COUPLING OF ARYL PHOSPHATES WITH GRIGNARD AND ORGANO-ALUMINUM REAGENTS - SYNTHESIS OF ALKYLBENZENES, ALKENYLBENZENES AND ARYLBENZENES FROM PHENOLS
TETRAHEDRON LETTERS
07/27/1981Csp2_ar-Csp3E-NuOAl
OP(O)(OEt)2
Al(Et)2ArylAlkylNo baseNo BaseStrong0.04_10.1021/ol9028308,10.1021/jo2000034,10.1021/jo00041a004,10.1021/ja710944j,10.1021/acscatal.9b00744,10.1002/anie.201402922,10.1021/ja210249h,10.1021/jo010452+,10.1021/ja903091g10.1055/a-1349-3543,10.1021/acs.orglett.0c01123,10.1002/cjoc.201900506,10.1002/ejoc.201901362,10.1021/acs.joc.9b00669,10.1021/acscatal.9b00744,10.1016/j.tet.2018.10.025,10.1002/jhet.3280,10.1021/acscatal.6b02964,10.1002/slct.201601789,10.1039/c6dt02995g,10.1055/s-0035-1560175,10.1016/j.tetlet.2015.10.009,10.1021/acs.joc.5b01540,10.1016/j.tetlet.2015.07.033,10.1002/ejoc.201500630,10.1002/adsc.201500304,10.1002/ajoc.201500044,10.1016/j.tetlet.2014.12.016,10.1002/anie.201402922,10.1021/op300236f,10.1039/c3ra44884c,10.1021/ol300908g,10.1021/ja210249h,10.1002/chem.201103304,10.1016/j.tetlet.2010.11.133,10.1021/jo2000034,10.1021/cr100259t,10.1021/cr100327p,10.1039/c1cs15100b,10.1002/chem.201002273,10.1021/ol1018739,10.1021/ol9028308,10.1055/s-0029-1219165,10.1021/ja903091g,10.1021/jo900098a,10.1016/j.tetlet.2008.10.138,10.1021/ja710944j,10.1039/b801888j,10.1021/ja072446m,10.1021/ja070321b,10.1007/s10600-006-0247-7,10.1107/S1600536806003643,10.1021/jo0520994,10.1016/j.tetlet.2005.06.016,10.1016/j.tet.2005.02.085,10.1016/j.tet.2004.12.033,10.1002/anie.200461444,10.1055/s-2004-834878,10.1016/S0040-4039(03)01804-5,10.1016/S0040-4039(03)00191-6,10.1246/bcsj.75.203,10.1002/hc.10006,10.1021/jo010452+,10.1016/S0040-4020(97)10233-2,10.1021/jo971636k,10.1016/S0040-4039(97)00187-1,10.1002/chem.19960021006,10.1021/jo960617s,10.1016/0040-4020(96)00246-3,10.1039/c39940001923,10.1016/S0040-4039(00)73192-3,10.1016/0040-4039(94)88017-4,10.1021/ja00068a092,10.1016/S0040-4020(01)87192-1,10.1039/p19920003419,10.1021/jm00103a003,10.1021/jo00041a004,10.1016/S0040-4039(00)77678-7,10.1016/S0040-4039(00)94557-X,10.1021/ja00203a066,10.1021/ja00225a037,10.1016/S0040-4020(01)85098-5,10.1016/S0040-4020(01)86177-9,10.1016/S0040-4039(00)80811-4,10.1016/0022-328X(87)87187-5,10.1021/ja00252a029,10.1021/jo00378a033,10.1021/jo00370a006,10.1016/0022-328X(84)80563-X,10.1021/ja00313a032,10.1016/S0022-328X(00)99425-7,10.1016/S0040-4039(00)94166-2checked by Kelly12/30/2021
140
87FALSEs-1994-2285010.1055/s-1994-22850https://sci-hub.wf/10.1055/s-1994-22850https://doi.org/10.1055/s-1994-22850NiC-O ActivationShihongTRUEx321621994Snieckus, V
#N/ASYNLETT#N/A#N/A5/1/1994Csp2_ar-Csp2_arE-NuOZnOTfZnXArylArylNo baseNo BaseWeak0.53_1/25/2022
141
132FALSEs0040-4039(97)00178-010.1016/s0040-4039(97)00178-0https://sci-hub.wf/10.1016/s0040-4039(97)00178-0https://doi.org/10.1016/s0040-4039(97)00178-0NiC-O ActivationKelly7-FebTRUE668581997
RajanBabu, T.V
Nickel-catalyzed asymmetric allylation of alkyl Grignard reagents. Effect of ligands, leaving groups and a kinetic resolution with a hard nucleophile
TETRAHEDRON LETTERS
Enantioselective addition of Grignard reagents to methyl 1,3-diphenylallyl ether in the presence of Ni(0)-phosphine catalysts is reported Kinetic resolution (79 %ee) observed in the addition of MeMgBr has important implications for the mechanism and further development of this reaction as a valuable synthetic reaction. (C) 1997 Elsevier Science Ltd.
RajanBabu, T.V3/10/1997Csp3-Csp3E-NuOMgOMeMgXAllylAlkylNo baseNo BaseStrong-0.28_xx10.1021/ol702122d,10.1039/c1sc00026h,10.1021/ja3013825,10.1021/ol4031364,10.1002/chem.201502329,10.1021/ja710944j,10.1039/b002547j,10.1021/ja300031w10.1002/ejic.202100820,10.6023/cjoc202106021,10.1021/acs.orglett.1c02938,10.1021/acscatal.1c03449,10.1021/acs.inorgchem.1c01720,10.1039/d1sc02547c,10.1021/acs.orglett.0c04316,10.1002/anie.202008071,10.1021/acs.chemrev.9b00682,10.1002/anie.201915454,10.1021/acs.orglett.0c01109,10.1021/acs.orglett.9b03633,10.6023/cjoc201809037,10.1039/c8cc07093h,10.1002/cjoc.201800237,10.1246/cl.170533,10.1021/acs.orglett.7b00473,10.1002/anie.201609654,10.1016/j.jorganchem.2016.05.014,10.1002/chem.201502329,10.1021/acs.chemrev.5b00162,10.1021/acs.orglett.5b00654,10.1021/ol4031364,10.1021/ja3079362,10.1021/ol3009842,10.1021/ja3013825,10.1021/ja300031w,10.1007/3418_2011_15,10.1002/asia.201000875,10.1021/ol2012007,10.1002/anie.201104390,10.1039/c1sc00026h,10.1021/ar100082d,10.1055/s-0029-1217368,10.1055/s-2008-1077903,10.1021/ja710944j,10.1002/anie.200605113,10.1021/ol702122d,10.1021/ol0713842,10.5059/yukigoseikyokaishi.65.761,10.1021/ja0730718,10.1021/jo0625655,10.1021/ja067456m,10.1039/b513887f,10.1021/ja0469030,10.1002/anie.200460842,10.1073/pnas.0307271101,10.1002/adsc.200303207,10.1021/om010343l,10.1016/S0040-4039(00)01448-9,10.1016/S0022-328X(00)00173-X,10.1016/S0040-4020(99)00965-5,10.1039/a908076g,10.1002/(SICI)1521-3765(20000117)6:2<353::AID-CHEM353>3.0.CO;2-U,10.1039/b002547j,10.1039/a906654f,10.1021/jo982438b,10.1039/a803242d,10.1021/ja981560p,10.1021/ja980499l,10.1246/bcsj.71.973,10.1016/S0040-4020(97)10217-4checked by Kelly1/16/2022
142
131FALSEs0040-4039(99)00517-110.1016/s0040-4039(99)00517-1https://sci-hub.wf/10.1016/s0040-4039(99)00517-1https://doi.org/10.1016/s0040-4039(99)00517-1NiC-O ActivationLongTRUE645581999Yang, Z
Nickel-catalyzed cross-couplings of cyclohexenyl phosphate and arylboronic acids
TETRAHEDRON LETTERS
The Nickel-catalyzed cross-coupling reaction of cyclohexenylphosphate with a variety of arylboronic acids is described here for the first time. This methodology opens the door to other palladium or nickel-catalyzed coupling reactions involving vinyl phosphates. (C) 1999 Elsevier Science Ltd. All rights reserved.
Harvard Univ4/23/1999Csp2_ar-Csp2_arE-NuOB
OPO(OPh)2
B(OH)2ArylArylK3PO4Ionic-PO4Strong0.04_10.1021/jo2000034,10.1021/jo070912k,10.1021/jacs.8b02134,10.1039/b609064h,10.1021/jo010452+10.1021/acs.joc.0c01254,10.1002/aoc.5662,10.1039/c8ob01533c,10.1021/jacs.8b02134,10.1002/slct.201601789,10.1002/chem.201602150,10.1007/s12039-016-1111-3,10.1080/00958972.2016.1186800,10.1055/s-0035-1560175,10.1016/j.tetlet.2015.10.009,10.1002/ajoc.201500044,10.1055/s-0033-1339509,10.1080/10426507.2012.704103,10.1039/c3cs35521g,10.1055/s-0031-1289717,10.1002/chem.201103304,10.1002/anie.201203778,10.1021/ja207759e,10.1016/j.tetlet.2010.11.133,10.1021/jo2000034,10.1021/cr100259t,10.1021/cr1002276,10.1002/rcm.4847,10.1039/c1cs15100b,10.1002/chem.201002273,10.1080/17415993.2011.628991,10.1055/s-0030-1259104,10.1007/s00706-009-0199-2,10.1055/s-0029-1217964,10.1021/jo900098a,10.1002/anie.200903146,10.1080/00958970802483624,10.1016/j.tetlet.2008.04.116,10.1039/b801888j,10.1039/b705664h,10.1021/jo070912k,10.1021/ja070321b,10.1016/j.poly.2006.10.006,10.1021/jo0607360,10.1002/anie.200600442,10.1039/b609064h,10.1016/j.tetlet.2005.08.136,10.1021/ol0517271,10.1016/j.tetlet.2005.03.203,10.1055/s-2004-830860,10.1039/b411111g,10.2174/0929867033456738,10.1016/S0040-4039(03)00873-6,10.1021/cc020045r,10.1016/S0040-4020(02)01188-2,10.1016/S0040-4020(02)00826-8,10.1016/S0040-4020(02)00045-5,10.1016/S0010-8545(01)00401-5,10.1021/jo010452+,10.1007/BF03184324,10.5059/yukigoseikyokaishi.59.193,10.1021/ol990885n,10.1016/S0040-4039(99)01255-1,10.1021/ja990432dchecked by Kelly12/15/2021
143
317FALSEacs.accounts.5b00051
10.1021/acs.accounts.5b00051
https://sci-hub.wf/10.1021/acs.accounts.5b00051https://doi.org/10.1021/acs.accounts.5b00051NiC-O ActivationWilliam20-JulyTRUE5011#N/A2015
ACCOUNTS OF CHEMICAL RESEARCH
Csp3-Csp3E-NuOMgOMeMgXAlkylAlkylNo baseNo BaseStrong-0.287/28/2022
144
127FALSEacs.joc.5b0013510.1021/acs.joc.5b00135https://sci-hub.wf/10.1021/acs.joc.5b00135https://doi.org/10.1021/acs.joc.5b00135NiC-O ActivationKellyTRUE6511852015
Molander, GA
Engaging Nonaromatic, Heterocyclic Tosylates in Reductive Cross-Coupling with Aryl and Heteroaryl Bromides
JOURNAL OF ORGANIC CHEMISTRY
A method has been developed for the introduction of nonaromatic heterocyclic structures onto aryl and heteroaryl bromides using alkyl tosylates in a reductive cross-coupling manifold. This protocol offers an improvement over previous methods by utilizing alkyl tosylate coupling partners that are bench-stable, crystalline solids that can be prepared from inexpensive, commercially available alcohols.
Univ Penn3/6/2015Csp3-Csp2_arE-EOXOTsBrAlkylAryl#N/ANo BaseWeak0.36_10.1021/acscatal.1c05208,10.1021/jacs.9b05224,10.1039/c9sc03347e,10.1021/jacs.0c01330,10.1021/jacs.0c13093,10.1039/c7cc01932g,10.1039/c7sc03140h,10.1021/acs.orglett.9b01014,10.1021/jacs.7b02389,10.1021/acs.orglett.9b00174,10.1021/acscatal.1c0520810.1055/s-0041-1737762,10.1021/acscatal.1c05208,10.1021/jacs.1c11170,10.1002/anie.202112876,10.1021/acs.orglett.1c02893,10.1021/acs.orglett.1c02874,10.1021/acs.joc.1c01073,10.1021/jacs.1c03459,10.1021/jacs.0c13093,10.1021/acscatal.0c03237,10.1021/acsomega.0c04181,10.1021/acscatal.0c01842,10.1021/jacs.0c04812,10.1021/jacs.0c02673,10.1021/jacs.0c01330,10.1039/c9cc09377j,10.1002/chem.201904545,10.1039/c9sc03347e,10.1016/j.tetlet.2019.150991,10.1021/jacs.9b05224,10.1021/acs.orglett.9b01987,10.1021/acs.orglett.9b01097,10.1021/acs.orglett.9b01014,10.1021/acs.orglett.9b00174,10.1021/jacs.8b13534,10.1021/acs.orglett.8b02498,10.1016/j.bmcl.2018.06.038,10.3390/molecules23061449,10.1038/s41557-018-0021-z,10.1002/ajoc.201700681,10.1055/s-0036-1591853,10.1039/c7sc03140h,10.1016/bs.aihch.2017.10.001,10.1002/anie.201706781,10.1055/s-0036-1588464,10.1039/c7cc04252c,10.1021/acs.joc.7b01334,10.1039/c7cc01932g,10.1021/jacs.7b02389,10.1055/s-0036-1588132,10.1002/anie.201607959,10.1038/NCHEM.2587,10.1021/jacs.6b09533,10.1021/acs.orglett.6b02665,10.1055/s-0035-1562442,10.1021/acs.orglett.6b01837,10.1007/s41061-016-0042-2,10.1021/acscatal.6b00841,10.1021/jacs.6b00250,10.1002/anie.201509341,10.1039/c6ob02269c,10.1039/c6ob00936k,10.1021/acs.orglett.5b02572,10.1021/jacs.5b06255,10.1002/chem.201501543,10.1021/jacs.5b06466,10.1002/ejoc.201500784,10.1039/c5qo00224aKelly1/11/2022
145
290FALSEacs.joc.6b0080010.1021/acs.joc.6b00800https://sci-hub.wf/10.1021/acs.joc.6b00800https://doi.org/10.1021/acs.joc.6b00800NiC-O ActivationxWilliam29-MayTRUE371852016Molander, GA
Phenol Derivatives as Coupling Partners with Alkylsilicates in Photoredox/Nickel Dual Catalysis
JOURNAL OF ORGANIC CHEMISTRY
Photoredox/nickel dual catalysis via single electron transmetalation allows coupling of C-sp(3)-C-sp(2) hybridized centers under mild conditions. A procedure for the coupling of electron deficient aryltriflates, -tosylates, and -mesylates with alkylbis-(catecholato)silicates is presented. This method represents the first example of the use of phenol derivatives as electrophilic coupling partners in photoredox/nickel dual catalysis.
8/19/2016Csp2_ar-Csp3E-EOSiOTf
2,2'-spirobi[benzo[d][1,3,2]dioxasilole]
ArylAlkylNo baseNo BaseWeak0.536/15/2022
146
45FALSEacs.joc.6b0162710.1021/acs.joc.6b01627https://sci-hub.wf/10.1021/acs.joc.6b01627https://doi.org/10.1021/acs.joc.6b01627NiC-O ActivationGerryTRUE324892016Chatani, N
Nickel/N-Heterocyclic Carbene-Catalyzed Suzuki-Miyaura Type Cross-Coupling of Aryl Carbamates
JOURNAL OF ORGANIC CHEMISTRY
The utility of N-heterocyclic carbene ligands in nickel catalyzed Suzuki-Miyaura cross-coupling of aryl esters and carbamates is investigated. Imidazol-2-ylidene bearing 2-adarnarityl groups at its nitrogen atoms generates the most active nickel species among the ligands examined, allowing cross-coupling of a range of aryl carbamates and pivalates. Unlike the previously reported system using tricydohexylphosphine, this protocol is suitable for the cross-coupling using arylboronic esters in addition to arylboronic acids.
Osaka Univ10/7/2016Csp2_ar-Csp2_arE-NuOB
OCONEt2
B(nep)ArylArylK3PO4Ionic-PO4Medium0.31TMx10.1021/jacs.1c09797,10.1021/jacs.7b04973,10.1021/acscatal.8b03436,10.1021/acscatal.7b0105810.1021/jacs.1c09797,10.1016/j.mcat.2021.111500,10.1055/a-1349-3543,10.1002/chem.202004132,10.1016/j.jorganchem.2020.121543,10.1021/acs.chemrev.0c00088,10.1021/acsomega.9b04450,10.1007/s10562-019-02966-6,10.1039/c9dt00455f,10.1039/c8nj05503c,10.1021/acs.oprd.8b00325,10.1021/acscatal.8b03436,10.1016/j.tet.2018.10.025,10.1002/cctc.201800629,10.3390/molecules23071715,10.1016/j.jorganchem.2018.01.019,10.1021/acs.orglett.8b00674,10.1021/acs.orglett.7b03713,10.1002/ejoc.201701463,10.1016/j.mcat.2017.10.004,10.1002/ejoc.201701005,10.1021/jacs.7b04973,10.1248/cpb.c17-00487,10.1021/acscatal.7b01058,10.1039/c7cc00078b,10.1021/acs.orglett.6b03861,10.1246/bcsj.20160391,10.1039/c6cc08401j,10.1021/acscatal.6b029641/10/2022
147
49FALSEacs.joc.6b0256410.1021/acs.joc.6b02564https://sci-hub.wf/10.1021/acs.joc.6b02564https://doi.org/10.1021/acs.joc.6b02564NiC-O ActivationKellyTRUE34452017Wang, ZX
Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents
JOURNAL OF ORGANIC CHEMISTRY
Nickel-catalyzed cross-coupling of allyl alcohols with aryl- and alkenylzinc chlorides through C-O bond cleavage was performed. Reaction of (E)-3-phenylprop-2-en-1-ol and 1-aryl-prop-2-en-1-ols with aryl- or alkenylzinc chlorides gave linear cross-coupling products. Reaction of 1-phenyl- or 1-methyl-substituted (E)-3-phenylprop-2-en-1-ol with aryl- or alkenylzinc chlorides resulted in 3-aryl/alkenyl-substituted (E)-(prop-1-ene-1,3-diyl)dibenzenes or 3-aryl/alkenyl-substituted (E)-(but-1-enyl)benzene. Reaction of allyl alcohol with p-Me2NC6H4ZnCl resulted in a mixture of normal coupling product 4-allyl-N,N-dimethylaniline and its isomerized product N,N-dimethyl-4-(prop-1-en-1-yl)aniline.
Univ Sci & Technol China
5/5/2017Csp3-Csp2_arE-NuOZnOHZnXAllylArylNo baseNo BaseStrong-0.81_xxx10.1039/c7sc03140h,10.1021/acscatal.7b03079,10.1021/jacs.0c12462,10.1021/acscatal.0c0135610.6023/cjoc202106021,10.1021/acscatal.1c03729,10.1039/d1ob01874d,10.1039/d1cc05221g,10.1021/jacs.1c08695,10.1021/acs.orglett.1c02938,10.1039/d1sc02547c,10.1055/a-1467-2432,10.6023/cjoc202008012,10.1021/jacs.0c12462,10.1016/j.tet.2020.131493,10.1021/acs.chemrev.9b00682,10.1002/anie.202006322,10.1021/acscatal.0c01356,10.1002/anie.201915454,10.1021/acs.joc.0c00008,10.1002/anie.202000704,10.1021/acs.orglett.9b03633,10.1021/acs.orglett.9b02946,10.1039/c9qo00822e,10.3390/molecules24122296,10.1002/adsc.201801266,10.6023/cjoc201812051,10.6023/cjoc201809037,10.1002/ajoc.201800560,10.1021/acssuschemeng.8b02614,10.1002/cjoc.201800237,10.1039/c7sc03140h,10.1002/ajoc.201700515,10.2174/1570193X15666180220125122,10.1021/acscatal.7b03079,10.1039/c7cc08416a1/16/2022
148
269FALSEacs.joc.8b0260910.1021/acs.joc.8b02609https://sci-hub.wf/10.1021/acs.joc.8b02609https://doi.org/10.1021/acs.joc.8b02609NiC-O ActivationLong10-MarTRUE371262019Banerjee, D
Nickel-Catalyzed Alkylation of Ketone Enolates: Synthesis of Monoselective Linear Ketones
JOURNAL OF ORGANIC CHEMISTRY
Herein we have developed a Ni-catalyzed protocol for the synthesis of linear ketones. Aryl, alkyl, and heteroaryl ketones as well as alcohols yielded the monoselective ketones in up to 90% yield. The catalytic protocol was successfully applied in to a gram-scale synthesis. For a practical utility, applications of a steroid derivative, oleyl alcohol, and naproxen alcohol were employed. Preliminary catalytic investigations involving the isolation of a Ni intermediate and defined Ni-H species as well as a series of deuterium-labeling experiments were performed.
1/18/2019Csp3-ring(s)-Csp3E-NuOHOHHBenzylAlkylIonic-OtBuStrong-0.81_10.1039/d2qo00004k,10.1039/d1cy02159a,10.1021/acscatal.1c04732,10.1002/aoc.6493,10.1002/cctc.202101168,10.1021/acs.organomet.1c00328,10.1016/j.tetlet.2021.153270,10.1039/d1dt01704g,10.1021/acs.orglett.1c01765,10.1002/chem.202101360,10.1021/acs.orglett.1c00782,10.1039/d1ob00080b,10.1002/ajoc.202000686,10.1021/jacs.0c10055,10.1039/d0cy01679a,10.1039/d0dt02937h,10.7536/PC200607,10.1021/acs.orglett.0c02340,10.1002/cssc.202000576,10.3390/molecules25071590,10.1016/j.tet.2019.130640,10.1002/chem.201904095,10.1021/acs.joc.9b02064,10.1021/acs.joc.9b01600,10.1002/ajoc.201900438,10.1002/cssc.201900990,10.1021/acs.joc.9b015173/11/2022
149
73FALSEacs.organomet.5b0087410.1021/acs.organomet.5b00874https://sci-hub.wf/10.1021/acs.organomet.5b00874https://doi.org/10.1021/acs.organomet.5b00874NiC-O ActivationLongTRUE445252015Sun, HM
Mixed NHC/Phosphine Ni(II) Complexes: Synthesis and Their Applications as Versatile Catalysts for Selective Cross-Couplings of ArMgX with Aryl Chlorides, Fluorides, and Methyl Ethers
ORGANOMETALLICS
New methods for the preparation of mixed NHC/phosphine Ni(II) complexes have been developed. It was shown that the quaternary ammonium cation in the easily available Ni(II) complexes [NEt4] [Ni(PPh3)X-3] (X = Cl and Br) can act as a good leaving group in reactions of [NEt4][Ni(PPh3)X-3] with the bulky ItBu (ItBu = 1,3-ditertbutylimidazol-2-ylidene) or IPr [IPr = 1,3-bis (2,6-diisopropylphenyl)imidazol-2-ylidene] ligarid, resulting in the corresponding mixed NHC/PPh3 Ni(II) complexes Ni(PPh3)-(ItBu)X-2 (X = Cl, 1; X = Br, 2) or Ni(PPh3)(IPr)Br-2 (3) in high yields. The PPh3 ligand in these obtained mixed NHC/PPh3 Ni(II) complexes can be easily substituted by a more electron-donating phosphine ligand, i.e., PC)T, resulting in the corresponding mixed NHC/PCy3 Ni(II) complexes Ni(PCy3)(ItBu)Br-2 (4) and Ni(PCy3)(IPr)Br-2 (5) in high yields. The crystal structures of these NO) complexes have been characterized, which revealed a trans disposition of the NHC ligand to the phosphine ligand. The catalytic behaviors of them on varying the carbene ligand (ItBu vs IPr) as well as the phosphine ligand (PPh3 vs PCy3) were investigated in the cross-coupling of aryl Grignard reagents with a wide range of electrophiles. In addition to a significant synergic effect on their catalytic activities, high selectivity for the activation and transformation of C-Cl, C-F and C-O bonds was achieved based on the rational structural design. Complex 2 showed the highest catalytic activity for the cross, coupling of aryl chlorides and fluorides with aryl Grignard reagents, but exhibit little activity for the cross-coupling of aryl methyl ethers with aryl Grignard reagents. On contrast, complex 4 showed great potential for the aryl methyl ethers involved cross-coupling reactions, although its reactivity for the activation of the C-X bond is very poor. The difference in catalytic activity between 2 and 4 has been successfully employed to construct oligoarenes by selective cross-coupling reactions.
Soochow Univ12/28/2015Csp2_ar-Csp2_arE-NuOMgOMeMgXArylArylNo baseNo BaseStrong-0.28_10.1016/j.tet.2017.06.004,10.1002/ejic.201900692,10.1002/chem.201603436,10.1021/acscatal.7b03079,10.1021/acscatal.7b0105810.1007/s12039-021-01950-1,10.1002/tcr.202100204,10.1039/d1qo00549a,10.1055/a-1349-3543,10.1021/acs.organomet.0c00515,10.1021/acs.chemrev.0c00088,10.1002/aoc.5741,10.1246/bcsj.20190310,10.14102/j.cnki.0254-5861.2011-2331,10.1107/S2053229619012038,10.1002/ejic.201900692,10.1021/acs.orglett.9b01645,10.1021/acs.organomet.8b00878,10.1002/jhet.3504,10.1021/acs.chemrev.8b00505,10.1055/s-0037-1611663,10.1021/acs.chemrev.8b00361,10.1002/ejic.201801179,10.1007/3418_2018_19,10.1039/c8dt01295d,10.1038/s41467-018-03928-z,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.1070/RCR4795,10.1021/acscatal.7b03079,10.1248/cpb.c17-00487,10.1021/acs.organomet.7b00463,10.1016/j.tet.2017.06.004,10.1039/c7dt01805c,10.1021/acscatal.7b01058,10.1002/chem.201603436,10.1021/acs.organomet.6b00638,10.1007/s41061-016-0043-1,10.1021/acs.orglett.6b01134,10.1016/j.jorganchem.2016.02.005,10.1016/bs.adomc.2016.07.001,10.1039/c6dt03235d,10.1039/c6dt02995g1/6/2022
150
97FALSEs-1989-3470310.1055/s-1989-34703https://sci-hub.wf/10.1055/s-1989-34703https://doi.org/10.1055/s-1989-34703NiC-O ActivationLongTRUEx3511989Dixon, NJ
#N/ASYNLETT#N/A#N/A6/22/1989Csp3-Csp3E-NuOMgOPivMgXAlkylAllylNo baseNo BaseMedium0.33_cannot find in web of science1/19/2022
151
39FALSEacs.orglett.5b0024110.1021/acs.orglett.5b00241https://sci-hub.wf/10.1021/acs.orglett.5b00241https://doi.org/10.1021/acs.orglett.5b00241NiC-O ActivationGerryTRUE301172015Kalyani, D
Nickel-Catalyzed Decarboxylative Cross-Coupling of Perfluorobenzoates with Aryl Halides and Sulfonates
ORGANIC LETTERS
A Ni-catalyzed method for the coupling of perfluorobenzoates with aryl halides and pseudohalides is described. Aryl iodides, bromides, chlorides, triflates, and tosylates participate in these transformations to afford the products in good yields. Penta-, tetra-, and trifluorinated biaryl compounds are obtained using these newly developed Ni-catalyzed decarboxylative cross-coupling reactions.
St Olaf Coll3/6/2015yCsp2_ar-Csp2_arE-EOCsp2OTfCO2KArylArylNo baseNo BaseWeak0.53_xx10.1021/acscatal.7b0261810.1039/d1cc00202c,10.1039/d1cs00216c,10.1039/d0qo00923g,10.1021/acs.orglett.0c02215,10.1021/acsomega.9b04450,10.1002/slct.201902860,10.1002/aoc.5192,10.1055/s-0037-1609636,10.1002/adsc.201800729,10.1002/adsc.201800333,10.1246/cl.171212,10.1039/c7gc02949g,10.1021/acscatal.7b02618,10.1002/slct.201701438,10.1021/jacs.7b05155,10.1039/c7ob01466j,10.1002/adsc.201601407,10.1002/chem.201604496,10.1002/anie.201701918,10.1002/adsc.201600974,10.1039/c7ra05711c,10.1002/anie.201604329,10.1021/acs.joc.6b01041,10.1021/acs.joc.6b00883,10.1002/bkcs.10706,10.1021/acs.joc.5b02873,10.1039/c5qo00040h,10.1039/c5ra07771k1/10/2022
152
168FALSEacs.orglett.5b0220010.1021/acs.orglett.5b02200https://sci-hub.wf/10.1021/acs.orglett.5b02200https://doi.org/10.1021/acs.orglett.5b02200NiC-O ActivationLongTRUE9017892015Chatani, N
Nickel-Catalyzed Cross-Coupling of Anisoles with Alkyl Grignard Reagents via C-O Bond Cleavage
ORGANIC LETTERS
Nickel-catalyzed cross-coupling of methoxyarenes with alkyl Grignard reagents, which involves the cleavage of the C(aryl)-OMe bond, has been developed. The use of 1,3-dicyclohexylimidazol-2-ylidene as a ligand allows the introduction of a variety of alkyl groups, including Me, Me3SiCH2, ArCH2, adamantyl, and cyclopropyl. The method can also be used for the alkylative elaboration of complex molecules bearing a C(aryl)-OMe bond.
Osaka Univ9/4/2015TRUETRUECsp2_ar-Csp3E-NuOMgOMeMgXArylAlkylNo baseNo BaseStrong-0.28_xAdded by Long10.1246/cl.150936,10.1021/acs.organomet.5b00874,10.1021/acs.orglett.5b03151,10.1021/jacs.7b04279,10.1021/jacs.6b03253,10.1021/acs.orglett.6b02656,10.1021/acscatal.7b01058,10.1021/jacs.1c09797,10.1021/acscatal.8b03436,10.1021/acs.orglett.8b01062,10.1021/acs.joc.6b01627,10.1021/jacs.8b02134,10.1002/chem.201603436,10.1002/anie.201806790,10.1002/anie.201607646,10.1002/anie.201510497,10.1021/acscatal.6b0080110.1039/d1nj04796e,10.1021/jacs.1c09797,10.1002/adsc.202100585,10.1039/d1qo00549a,10.1021/acs.orglett.1c01053,10.1021/jacs.1c03038,10.1055/a-1467-2494,10.1021/acs.joc.0c02389,10.1039/d0qo00785d,10.1055/s-0040-1705986,10.1021/acs.orglett.0c03507,10.1021/acs.chemrev.0c00088,10.1021/acs.orglett.0c02609,10.1021/acs.orglett.0c02236,10.1039/d0sc01641a,10.1002/cjoc.201900506,10.1246/cl.200083,10.1021/jacs.0c00283,10.1002/jccs.201900450,10.1021/acs.joc.9b02554,10.6023/A19050193,10.1021/acs.orglett.9b02504,10.1002/adsc.201900745,10.1002/cctc.201900230,10.1002/anie.201902315,10.1021/acs.orglett.9b00946,10.1016/j.tetlet.2018.12.043,10.1007/3418_2018_19,10.1070/RCR4881,10.1021/acscatal.8b03436,10.1002/adsc.201801135,10.1021/acs.joc.8b02104,10.1021/acs.orglett.8b02351,10.1039/c8cc03665a,10.1002/anie.201806790,10.1021/acs.orglett.8b01696,10.1039/c8cc02325e,10.1021/acs.orglett.8b01062,10.1021/acs.orglett.8b00313,10.1021/acs.orglett.8b00674,10.1021/jacs.8b02134,10.1002/cjoc.201700664,10.1039/c7cy01205e,10.1070/RCR4795,10.1055/s-0036-1589093,10.1055/s-0036-1588568,10.1021/acs.orglett.7b03152,10.1248/cpb.c17-00487,10.1021/jacs.7b04279,10.1021/acscatal.7b01058,10.1002/ejoc.201700514,10.1021/acs.orglett.6b03861,10.1246/bcsj.20160391,10.1002/anie.201610409,10.1039/c6sc02895k,10.1021/acs.joc.6b02666,10.1021/acscatal.6b02964,10.1002/anie.201607646,10.1021/acs.orglett.6b02656,10.1002/ajoc.201600411,10.1002/chem.201604160,10.1016/j.jaap.2016.09.009,10.1246/cl.160712,10.1002/mrc.4477,10.1002/chem.201603436,10.1021/acs.organomet.6b00638,10.1021/acs.joc.6b01627,10.1002/asia.201600972,10.1007/s41061-016-0043-1,10.1021/acscatal.6b00801,10.1021/acs.orglett.6b01134,10.1021/jacs.6b03253,10.1002/anie.201510497,10.3762/bjoc.12.65,10.1016/j.tet.2016.02.005,10.1016/bs.adomc.2016.07.001,10.1039/c5qo00395d,10.1021/acs.joc.5b02557,10.1021/acs.organomet.5b00874,10.1021/acs.orglett.5b03151,10.1246/cl.150936,10.3762/bjoc.11.261,10.1021/jacs.5b08621,10.3762/bjoc.11.235Kelly11/9/2021
153
115FALSEacs.orglett.5b0315110.1021/acs.orglett.5b03151https://sci-hub.wf/10.1021/acs.orglett.5b03151https://doi.org/10.1021/acs.orglett.5b03151NiC-O ActivationShihongTRUE564892015Chatani, N
Nickel-Catalyzed Formal Homocoupling of Methoxyarenes for the Synthesis of Symmetrical Biaryls via C-O Bond Cleavage
ORGANIC LETTERS
A new method has been developed for the nickel-catalyzed homocoupling of methoxyarenes via bond cleavage using a diboron reagent The use of 1,3-dicyclohexylimidazol-2-ylidene as a ligand was found to be critical to the success of the reaction. This new method allows the synthesis of a wide range of biaryl compounds.
Osaka Univ12/18/2015Csp2_ar-Csp2_arE-EOOOMeOMeArylArylNaOtBuIonic-OtBuStrong-0.28_10.1021/jacs.1c09797,10.1021/jacs.7b04279,10.1021/acs.joc.6b01627,10.1021/jacs.7b0232610.1021/jacs.1c09797,10.1039/d1nj04008a,10.1002/anie.202106356,10.1039/d1qo00811k,10.1055/a-1509-5954,10.1021/jacs.1c03038,10.1055/a-1349-3543,10.1007/s41061-020-00316-4,10.1021/acs.chemrev.0c00088,10.1021/acs.orglett.0c02165,10.1021/acs.orglett.0c02236,10.1021/acs.orglett.0c01424,10.1021/acs.joc.0c00640,10.1002/cjoc.201900506,10.1021/jacs.0c02839,10.1021/jacs.9b12519,10.1002/chem.201904842,10.1039/c9ob00995g,10.1021/jacs.8b13534,10.1007/3418_2018_19,10.1039/c8cc08504h,10.1021/acs.orglett.8b02351,10.1246/cl.180361,10.1021/acs.orglett.8b00674,10.1021/acs.orglett.7b03753,10.1055/s-0036-1588548,10.1002/chem.201703266,10.1055/s-0036-1589093,10.1055/s-0036-1588568,10.1055/s-0036-1589120,10.1016/j.tetlet.2017.07.087,10.1021/jacs.7b04279,10.1039/c7cy01040k,10.1021/jacs.7b02326,10.1021/acs.orglett.6b03861,10.1021/jacs.7b00049,10.1246/bcsj.20160391,10.1002/anie.201611974,10.1002/anie.201610409,10.1021/acscatal.6b02964,10.1016/j.poly.2016.04.006,10.1246/cl.160712,10.1021/acs.organomet.6b00638,10.1021/acs.joc.6b01627,10.1055/s-0035-1562488,10.1002/asia.201600972,10.1021/acs.chemrev.6b00193,10.1002/asia.201600943,10.1007/s41061-016-0043-1,10.1002/adsc.201600336,10.1021/acs.orglett.6b01250,10.3762/bjoc.12.65,10.1016/bs.adomc.2016.07.001Kelly1/6/2022
154
5FALSEacs.orglett.6b0081910.1021/acs.orglett.6b00819https://sci-hub.wf/10.1021/acs.orglett.6b00819https://doi.org/10.1021/acs.orglett.6b00819NiC-O ActivationGerryTRUE517282016Shi, ZJ
C-O/C-H Coupling of Polyfluoroarenes with Aryl Carbamates by Cooperative Ni/Cu Catalysis
ORGANIC LETTERS
Cross-coupling of polyfluoroarenes with aryl carbamates through the cleavage of both sp(2) C-O and C-H bonds is reported, The reaction conditions are simple, and only transition-metal catalysts and ligands are essential. Mechanistic studies indicated that Ni catalyst played an important role in activating C-O bond, while the Cu one in activating C-H Bond. The developed system proved to be effective for cross-coupling of terminal alkynes with aryl carbamates.
Peking Univ6/3/2016TRUETRUEFALSEComplex is CuxyCsp2_ar-Csp2_arE-NuOH
OCONMe2
HArylArylNo baseNo BaseMedium0.31_xshihong added10.1021/acscatal.8b03436,10.1021/acscatal.7b02618,10.1021/acs.orglett.7b00831,10.1021/jacs.9b02751,10.1021/jacs.1c09797,10.1021/jacs.7b04973,10.1002/ejic.20190069210.1002/adsc.202101469,10.1021/acs.organomet.1c00578,10.1021/jacs.1c09797,10.1055/a-1349-3543,10.1021/acs.chemrev.0c00245,10.1021/acs.chemrev.0c00088,10.1002/asia.202000763,10.1039/d0sc01585g,10.1002/cjoc.201900506,10.1021/acs.joc.0c00141,10.1021/jacs.0c00283,10.1021/acsomega.9b04450,10.1039/c9cc08663c,10.1016/j.jcat.2019.07.026,10.1002/ejic.201900692,10.1002/chem.201900822,10.1039/c9gc00305c,10.1021/acs.orglett.9b00122,10.1021/acs.orglett.9b00072,10.1016/j.tet.2018.12.013,10.1007/3418_2018_19,10.3390/catal9010076,10.1021/acs.accounts.8b00408,10.1002/ajoc.201800610,10.1021/acscatal.8b03436,10.1016/j.tet.2018.10.025,10.1021/acs.joc.8b02104,10.1002/adsc.201800729,10.1021/jacs.8b04479,10.1016/j.jorganchem.2018.01.019,10.1002/cjoc.201700808,10.1021/acs.orglett.8b00674,10.1039/c7dt04560c,10.1021/acscatal.7b02618,10.1021/jacs.7b04973,10.1021/acs.orglett.7b01938,10.1021/acs.orglett.7b00831,10.1002/ejoc.201700514,10.1021/acscatal.7b00397,10.1016/j.tet.2017.02.021,10.1039/c6gc03465a,10.1246/bcsj.20160365,10.1002/anie.201610409,10.1021/acscatal.6b02964,10.1021/acs.orglett.6b01675,10.1002/adsc.201600590,10.1016/bs.adomc.2016.07.0012/23/2022
155
78FALSEacs.orglett.6b0139810.1021/acs.orglett.6b01398https://sci-hub.wf/10.1021/acs.orglett.6b01398https://doi.org/10.1021/acs.orglett.6b01398NiC-O ActivationShihongTRUE461492016Kirchner, K
Air-Stable Triazine-Based Ni(II) PNP Pincer Complexes As Catalysts for the Suzuki-Miyaura Cross-Coupling
ORGANIC LETTERS
Air-stable, thermally robust, and well-defined cationic Ni(II) PNP pincer complexes based on the 2,4-diaminotriazine scaffold are described. These complexes are active catalysts for the Suzuki-Miyaura cross-coupling of a wide range of aryl, heteroaryl (including benzoxazole, thiazole, pyridine, pyrimidine, thiazole), primary and secondary alkyl halides, and pseudohalides with different organoboronate reagents giving excellent to good isolated yields. Neutral deprotonated complexes seem to play a key role in the catalytic process.
Vienna Univ Technol
7/1/2016Csp3-Csp2_arE-NuOBOTsBF3KAlkylArylK3PO4Ionic-PO4Weak0.36TM10.1021/acs.joc.1c02806,10.1039/d1ra04478h,10.1002/chem.202102031,10.1021/acs.organomet.1c00033,10.1039/d0dt03593a,10.1021/acscatal.0c05557,10.1002/ejic.202001129,10.1007/s10562-020-03487-3,10.1038/s41929-020-00564-z,10.1002/ejoc.202000707,10.1021/acs.organomet.9b00834,10.1002/ejic.202000206,10.1016/j.ica.2020.119457,10.1021/acsomega.9b04450,10.1055/s-0039-1691487,10.1016/j.saa.2019.117708,10.1021/acs.organomet.9b00672,10.1016/j.jorganchem.2019.120943,10.1021/acs.organomet.9b00386,10.1021/acs.orglett.9b02910,10.1021/acs.organomet.9b00083,10.1021/acs.organomet.9b00026,10.1007/s10562-019-02652-7,10.1039/c9dt00205g,10.1021/acs.chemrev.8b00555,10.1039/c8nj05503c,10.1002/ejic.201801179,10.1080/00958972.2018.1540779,10.1002/adsc.201800729,10.1002/cctc.201702019,10.1038/s41929-018-0081-x,10.1021/acs.organomet.8b00005,10.1002/anie.201710053,10.1016/j.molstruc.2017.07.066,10.1002/adsc.201700438,10.1002/cctc.201700218,10.1016/j.tet.2017.04.034,10.1002/anie.201611318,10.1007/s00706-016-1878-4,10.1021/acscentsci.6b00283,10.1002/adsc.201600689,10.1002/anie.2016062181/6/2022
156
41FALSEacs.orglett.6b0265610.1021/acs.orglett.6b02656https://sci-hub.wf/10.1021/acs.orglett.6b02656https://doi.org/10.1021/acs.orglett.6b02656NiC-O ActivationGerryTRUE3311282016Shi, ZJ
Practical Cross-Coupling between O-Based Electrophiles and Aryl Bromides via Ni Catalysis
ORGANIC LETTERS
Cross-coupling of various O-based electrophiles with aryl bromides was developed through Ni-catalyzed C-O activation in the presence of magnesium. Beside carboxylates, carbamates, and ethers, phenols exhibited excellent reactivity under modified conditions. This chemistry was featured as a simple and environmentally benign process with low catalyst loading and easy manipulations. The method exhibited broad substrate scopes.
Peking Univ12/2/2016Csp2_ar-Csp2_arE-EOXOMeBrArylArylNo baseNo BaseStrong-0.28_xxxx10.1021/acs.orglett.7b00831,10.1021/jacs.0c12462,10.1021/acscatal.7b02817,10.1021/jacs.7b02326,10.1021/jacs.0c04670,10.1021/jacs.8b08779,10.1002/ejic.201900692,10.1039/c7sc03140h,10.1002/anie.201806790,10.1021/acs.orglett.9b00174,10.1039/c8sc00609a10.1021/jacs.0c12462,10.1055/a-1349-3543,10.1055/s-0040-1707342,10.1021/acs.joc.0c02266,10.1021/acs.chemrev.0c00088,10.1021/acs.orglett.0c02236,10.1021/jacs.0c04670,10.1016/j.tetlet.2019.150991,10.1002/cjoc.201800554,10.1002/ejic.201900692,10.1039/c9ob00628a,10.1021/acs.orglett.9b00174,10.1055/s-0037-1611663,10.1021/jacs.8b13534,10.1007/3418_2018_19,10.1021/acs.joc.8b02104,10.1021/jacs.8b08779,10.1002/adsc.201800729,10.1002/anie.201806790,10.1039/c8sc00609a,10.1002/ajoc.201700450,10.1039/c8cc00001h,10.1039/c7sc03140h,10.1039/c7cy01205e,10.1055/s-0036-1588568,10.1021/acscatal.7b02817,10.1021/acs.orglett.7b00831,10.1021/jacs.7b023261/5/2022
157
167FALSEjacs.8b0877910.1021/jacs.8b08779https://sci-hub.wf/10.1021/jacs.8b08779https://doi.org/10.1021/jacs.8b08779NiC-N ActivationYizhouTRUE1604#N/A2018
Fang, HY; Shi, ZJ
Ni-Catalyzed Cross-Coupling of Dimethyl Aryl Amines with Arylboronic Esters under Reductive Conditions
J AM CHEM SOC
Herein, we reported a successful Suzuki-Miyaura coupling of dimethyl aryl amines to forge biaryl skeleton via Ni catalysis in the absence of directing groups and preactivation. This transformation proceeded with high efficiency in the presence of magnesium. Preliminary mechanism studies demonstrated dual roles of magnesium: (i) a reductant that reduced Ni(II) species to active Ni(I) catalyst; (ii) a unique promoter that facilitated the Ni(I)/Ni(III) catalytic cycle.
Fudan Univ10/24/2018TRUETRUEFALSECsp2_ar-Csp2_arE-NuNBNMe2B(nep)ArylArylNo baseNo Base_x10.1021/acscatal.8b04267,10.1021/acs.orglett.9b00242,10.1002/anie.202012048,10.1021/jacs.1c0979710.1021/acs.orglett.1c03590,10.1021/jacs.1c09797,10.1021/acs.orglett.1c03223,10.1039/c9cs00571d,10.1002/cctc.202100672,10.1021/acs.orglett.1c01503,10.1002/ajoc.202100044,10.1039/d1cc00203a,10.1039/d1gc00141h,10.1021/acs.joc.0c02992,10.1021/acs.organomet.0c00679,10.1021/acs.orglett.0c03660,10.1002/anie.202012048,10.1021/acs.joc.0c02266,10.1021/acscatal.0c03341,10.1021/acscatal.0c03334,10.1021/acscatal.0c02990,10.1021/acs.orglett.0c02367,10.1002/adsc.202000531,10.1021/jacs.0c05730,10.1021/acs.orglett.0c01869,10.1039/d0ra02195d,10.1016/j.catcom.2020.106009,10.1021/acs.joc.0c00491,10.1021/acs.organomet.9b00834,10.1002/cjoc.201900468,10.1021/acs.orglett.0c00679,10.1021/acs.orglett.0c00736,10.1002/chem.202000412,10.1016/j.tetlet.2020.151647,10.1021/acs.joc.9b03168,10.1039/c9qo01177c,10.1021/acscatal.9b04353,10.1038/s41467-019-13701-5,10.1039/c9dt03266e,10.1021/acs.orglett.9b03393,10.1002/anie.201908336,10.1021/acs.joc.9b01103,10.3390/molecules24183222,10.1021/acscatal.9b02440,10.1002/ejoc.201900940,10.1021/acs.organomet.9b00237,10.1021/acs.organomet.9b00060,10.1039/c9sc01083a,10.1039/c8cy02427h,10.1002/chem.201900886,10.1039/c9gc00289h,10.1021/acs.inorgchem.8b03489,10.1021/acs.orglett.9b00242,10.1021/acscatal.8b04267,10.1021/jacs.8b08792Long11/3/2021OCT 242018FALSEFALSEFALSEFALSE1404213575
158
53FALSEacs.orglett.7b0055610.1021/acs.orglett.7b00556https://sci-hub.wf/10.1021/acs.orglett.7b00556https://doi.org/10.1021/acs.orglett.7b00556NiC-O ActivationShihongTRUE354892017Rueping, M
Nickel-Catalyzed Synthesis of Primary Aryl and Heteroaryl Amines via C-O Bond Cleavage
ORGANIC LETTERS
A nickel-catalyzed protocol for the conversion of aryl and heteroaryl alcohol derivatives to primary and secondary aromatic amines via C(sp(2))-O bond cleavage is described. The new amination protocol can be applied to a range of substrates bearing diverse functional groups and uses readily available benzophenone imines as an effective nitrogen source.
Rhein Westfal TH Aachen
4/7/2017Csp2_ar-Nsp3E-NuOHOPivHArylNH2Cs2CO3Ionic-CO3Medium0.33_10.1021/acs.orglett.8b01021,10.1002/chem.201702867,10.1021/jacs.7b04973,10.1021/acscatal.8b0343610.1055/a-1548-8362,10.1039/d1qo00811k,10.1021/acs.orglett.1c00313,10.1021/acs.chemrev.0c01236,10.1021/acs.inorgchem.0c02127,10.1021/acscatal.0c03334,10.1021/acs.chemrev.0c00088,10.1002/chem.202002800,10.1246/cl.200099,10.1002/chem.201904842,10.1002/chem.201904288,10.1007/s11696-019-00734-9,10.1055/s-0037-1611732,10.1039/c9nj01748h,10.1002/cjoc.201800575,10.1002/adsc.201801661,10.1007/3418_2018_19,10.1021/acscatal.8b03436,10.1002/adsc.201800729,10.1021/jacs.8b04479,10.1016/j.jorganchem.2018.01.019,10.1021/acs.orglett.8b01021,10.1021/acs.orglett.8b00060,10.1039/c7cc08709h,10.1021/acs.orglett.7b03669,10.1055/s-0036-1591495,10.1021/acs.joc.7b02363,10.1002/ajoc.201700464,10.1021/jacs.7b04973,10.1002/chem.201702867,10.1021/acs.orglett.7b01905,10.1055/s-0036-15908191/5/2022
159
291FALSEacs.orglett.7b0158810.1021/acs.orglett.7b01588https://sci-hub.wf/10.1021/acs.orglett.7b01588https://doi.org/10.1021/acs.orglett.7b01588NiC-O ActivationxWilliam30-MayTRUE551852017Molander, GA
Direct Conversion of Carboxylic Acids to Alkyl Ketones
ORGANIC LETTERS
An efficient and mild method for acyl-C-sp3 bond formation based on the direct conversion of carboxylic acids has been established. This protocol is enabled by the synergistic, Ir-photoredox/nickel catalytic cross-coupling of in situ activated carboxylic acids and alkyltrifluoroborates. This versatile method is amenable to the cross-coupling of structurally diverse carbokylic acids with various potassium alkyltrifluoroborates, affording the corresponding ketones with high yields. In this operationally simple cross-coupling protocol, aliphatic ketones are obtained in one step from bench stable, readily available carboxylic acids.
7/7/2017yCsp2-Csp3E-NuOBOHBF3K
Carbonyl
AlkylNo baseNo BaseStrong-0.816/9/2022
160
271FALSEacs.orglett.8b0336710.1021/acs.orglett.8b03367https://sci-hub.wf/10.1021/acs.orglett.8b03367https://doi.org/10.1021/acs.orglett.8b03367NiC-O ActivationGerry12-MarTRUE436312018Ukaji, Y
Nickel-Catalyzed Cross-Electrophile Coupling between Benzyl Alcohols and Aryl Halides Assisted by Titanium Co-reductant
ORGANIC LETTERS
A nickel-catalyzed cross-electrophile coupling reaction between benzyl alcohols and aryl halides has been developed using a homolytic C-O bond cleavage protocol that has recently been established. The treatment of a benzyl alcohol and aryl halide with a nickel catalyst and low-valent titanium reagent generated from TiCl4(lutidine) (lutidine = 2,6-lutidine) and manganese powder afforded the cross-coupled product in high yield. A mechanistic study indicated the intermediacy of the benzyl radicals that originate from the benzyl alcohols.
12/21/2018Csp3-ring(s)-Csp2_arE-EOXOHIBenzylArylNo baseNo BaseStrong-0.81_10.1021/jacs.9b05224,10.1021/acs.orglett.9b00174,10.1021/jacs.0c12462,10.1021/acscatal.1c05208,10.1021/jacs.0c13093,10.1021/acscatal.1c0520810.1002/anie.202116775,10.1021/acscatal.2c00133,10.1021/acscatal.1c05530,10.1021/acscatal.1c05208,10.1021/acscatal.1c04239,10.6023/cjoc202106021,10.1039/d1ob01874d,10.1021/acs.orglett.1c02893,10.1016/j.chempr.2021.09.006,10.1021/acs.joc.1c01790,10.1038/s41586-021-03920-6,10.1002/ejoc.202100286,10.1246/bcsj.20200364,10.1055/a-1467-2432,10.1055/a-1406-0484,10.1021/jacs.0c13093,10.1021/acs.joc.0c01233,10.1021/acs.orglett.0c04039,10.1021/jacs.0c12462,10.1002/adsc.202000945,10.1055/s-0040-1707269,10.1021/acs.accounts.0c00291,10.1039/d0sc02948c,10.1039/d0sc01471k,10.1016/j.tetlet.2020.151729,10.1021/jacs.0c01475,10.1021/acs.orglett.0c00561,10.1039/c9cc07072a,10.1039/c9ra08930f,10.1021/acs.orglett.9b03102,10.1016/j.tetlet.2019.150991,10.1021/jacs.9b05224,10.1039/c9ob00628a,10.1021/acs.orglett.9b001743/14/2022
161
277FALSEacs.orglett.9b0017410.1021/acs.orglett.9b00174https://sci-hub.wf/10.1021/acs.orglett.9b00174https://doi.org/10.1021/acs.orglett.9b00174NiC-O ActivationShihong16-MarTRUE35312019Gong, HG
Ni-Catalyzed Reductive C-O Bond Arylation of Oxalates Derived from alpha-Hydroxy Esters with Aryl Halides
ORGANIC LETTERS
A Ni-catalyzed reductive cross-coupling of alpha-hydroxycarbonyl compounds modified with oxalyl groups and aryl halides has been developed that furnishes alpha-aryl esters under mild conditions and tolerates a variety of functionalized aryl halides bearing electron withdrawing and-donating groups. This work highlights C-O bond fragmentation on secondary alkyl carbon centers that generates alpha-carbonyl radicals.
3/15/2019Csp3-Csp2_arE-EOX
Monomethyl Oxalate
BrAlkylArylpyridineNitrogenNitrogen(neutral)Strong0.13_10.1021/acscatal.1c05208,10.1021/acscatal.1c05208,10.1021/jacs.0c1309310.1055/s-0040-1719881,10.1055/s-0041-1737762,10.1021/acs.joc.1c02897,10.1021/acs.orglett.1c04029,10.1021/acscatal.1c05208,10.1021/acs.orglett.1c03674,10.1039/d1qo01614h,10.1021/acscatal.1c04239,10.6023/cjoc202106021,10.1021/jacs.1c08695,10.1039/c9cs00571d,10.1016/j.tetlet.2021.153129,10.1002/ejoc.202100344,10.1021/jacs.0c13093,10.1021/acs.orglett.0c04039,10.1055/s-0040-1707342,10.1055/a-1328-0352,10.1021/jacs.0c07492,10.1021/acs.accounts.0c00291,10.1021/acscatal.0c01842,10.1021/jacs.0c04695,10.1002/ejoc.202000142,10.1021/acs.orglett.0c00561,10.1039/c9cc07072a,10.1016/j.trechm.2019.08.004,10.1021/acs.joc.9b01387,10.1016/j.tetlet.2019.1509913/17/2022
162
38FALSEacs.orglett.9b0116410.1021/acs.orglett.9b01164https://sci-hub.wf/10.1021/acs.orglett.9b01164https://doi.org/10.1021/acs.orglett.9b01164NiC-O ActivationKellyTRUE35102019Shu, XZ
Enones from Acid Fluorides and Vinyl Triflates by Reductive Nickel Catalysis
ORGANIC LETTERS
A nickel-catalyzed reductive coupling between acid fluorides and vinyl triflates has been described. This method provides an efficient access to various enones and avoids the requirement for acyl or vinyl metallic reagents in the conventional approaches. The reaction proceeds with a broad range of acid fluorides and cyclic vinyl triflates, tolerating several functional groups. The utility of this synthetic method has been demonstrated by the late-stage modification of pharmaceuticals and biologically active natural compounds.
Lanzhou Univ5/17/2019yCsp2-Csp2E-EOXOTfFVinyl
Carbonyl
No baseNo BaseWeak0.53_xxx10.1002/anie.20200227110.1039/d2sc00147k,10.1021/jacs.1c05670,10.1246/bcsj.20210148,10.1016/j.tetlet.2021.153129,10.1039/d1cc01381e,10.1016/j.rser.2021.111103,10.1002/tcr.202100053,10.1021/acs.orglett.1c00190,10.1002/anie.202014660,10.1055/s-0040-1707342,10.1016/j.tetlet.2020.152624,10.1021/acs.orglett.0c03342,10.1021/jacs.0c09949,10.1055/s-0040-1705954,10.1039/d0ra07472a,10.1002/chem.202001374,10.1039/d0cc03309j,10.1021/acs.orglett.0c01683,10.1021/acs.joc.0c00640,10.1002/cctc.201902290,10.1002/anie.202002271,10.1055/s-0039-1691525,10.1002/asia.202000117,10.1021/acs.joc.9b02785,10.1002/anie.201909543,10.1002/chem.201903668,10.1039/c9cc05325e2/7/2022
163
20FALSEacscatal.0c0029110.1021/acscatal.0c00291https://sci-hub.wf/10.1021/acscatal.0c00291https://doi.org/10.1021/acscatal.0c00291NiC-O ActivationShihongTRUE111492020Yamaguchi, J
Ester Transfer Reaction of Aromatic Esters with Haloarenes and Arenols by a Nickel CatalystACS CATALYSIS
A catalytic ester transfer reaction of aromatic esters with aryl halides/arenols was developed. The present reaction can transfer an ester functional group from certain aromatic esters to haloarenes. This ester transfer reaction involves two oxidative additions-one from the C-C bond of the aromatic ester and one from the C-halogen bond of haloarenes-onto a nickel catalyst. The utilization of a Ni/dcypt catalyst capable of cleaving both chemical bonds was a key for the reaction progress. Furthermore, naphthol-based aryl electrophiles were also applicable to the catalytic system via C-O bond activation.
Waseda Univ3/6/2020TRUEFALSEFALSECsp2_ar-Csp2E-EOCsp2OHpyridylAryl
Carbonyl
No baseNo BaseStrong-0.81_xxxx10.1038/s41929-020-00560-310.1039/d2ob00008c,10.1039/d1sc06968c,10.1039/d1ob01707a,10.1021/acs.orglett.1c03232,10.1021/jacs.1c04215,10.1021/jacs.1c00529,10.1038/s41929-020-00560-311/5/2021MAR 62020FALSEFALSEFALSEFALSE1053490
164
300FALSEacscatal.0c0119910.1021/acscatal.0c01199https://sci-hub.wf/10.1021/acscatal.0c01199https://doi.org/10.1021/acscatal.0c01199NiC-O ActivationxWilliam12-JunTRUE351452020Doyle, AG
Regioselective Cross-Electrophile Coupling of Epoxides and (Hetero)aryl Iodides via Ni/Ti/Photoredox CatalysisACS CATALYSIS
A cross-electrophile coupling reaction of epoxides and (hetero)aryl iodides that operates via the merger of three catalytic cycles involving a Ni-, Ti-, and organic photoredox catalyst has been developed. Three distinct classes of epoxides, styrene oxides, cyclic epoxides, and terminal aliphatic epoxides, all undergo coupling in moderate to good yield and high regioselectivity with the use of three different nitrogen-based ligands for Ni under otherwise identical reaction conditions. The mild reaction conditions accommodate a broad scope of abundant and complex coupling partners. Mechanistic studies suggest that when styrene oxides are employed radical intermediates are involved via Ti-radical ring-opening of the epoxide. Conversely, for terminal aliphatic epoxides, involvement of an iodohydrin intermediate enables the formation of the unexpected linear product.
5/15/2022Csp3-Csp2_arE-EOX
O(Ring-Opening)
XAlkylArylEt3NNitrogenNitrogen(neutral)Weak16/15/2022
165
175FALSEc3ob41989d10.1039/c3ob41989dhttps://sci-hub.wf/10.1039/c3ob41989dhttps://doi.org/10.1039/c3ob41989dNiC-N ActivationGerryTRUE54752013Wang, ZX
Nickel-catalyzed cross-coupling of aryltrimethylammonium triflates and amines
ORG BIOMOL CHEM
Nickel-catalyzed cross-coupling of aryltrimethylammonium triflates and amines was carried out under mild conditions. The reaction has a broad scope of substrates and can be performed by a one-pot procedure from an aryldimethylamine.
Univ Sci & Technol China
12/4/2013Csp2_ar-Nsp3E-NuNH
NMe3+OTf-
HAryl
Morpholine
NaOtBuIonic-OtBuE-H_xxx10.1039/c4qo00321g,10.1002/ajoc.201700569,10.1016/j.tet.2017.06.004,10.1002/anie.201511197,10.1021/om500452c,10.1038/NCHEM.2388,10.1038/nature1461510.1016/j.tet.2021.132431,10.1021/acs.orglett.1c02280,10.1021/acs.joc.1c01339,10.1016/j.fuel.2021.121377,10.1039/d1qo00759a,10.1039/d1sc00757b,10.1021/acs.joc.0c02992,10.1021/acscatal.0c03341,10.1002/ajoc.202000334,10.1039/d0nj01139h,10.1039/c9ob02667c,10.1039/c9ob02107h,10.1021/acs.orglett.9b02820,10.1016/j.tet.2019.07.007,10.1021/acs.oprd.9b00235,10.1021/acs.oprd.9b00194,10.1016/j.isci.2019.04.038,10.1039/c9sc01083a,10.1021/acscatal.9b00218,10.1021/acs.joc.8b02926,10.1021/acs.joc.8b02567,10.1039/c8cc07093h,10.6023/cjoc201803013,10.1038/s41467-018-05637-z,10.1039/c8ob00488a,10.6023/cjoc201710034,10.1055/s-0036-1588548,10.1002/ajoc.201700569,10.1002/ajoc.201700550,10.1002/asia.201701342,10.1002/ijch.201700044,10.3184/174751917X15094552081206,10.1016/j.tet.2017.06.004,10.1021/jacs.7b05273,10.6023/cjoc201612014,10.1021/acscatal.6b03277,10.1039/c7ra10755b,10.1039/c7ra02549a,10.1002/anie.201600697,10.1002/anie.201511197,10.1039/c6ob01307d,10.1039/c6cc04531f,10.1021/acs.joc.5b02557,10.1038/NCHEM.2388,10.1002/chem.201503596,10.1021/acs.chemrev.5b00386,10.1038/nature14615,10.1039/c4qo00321g,10.2174/1570178612666150203005106,10.1021/om500452c,10.1515/hc-2014-0096,10.1021/ja501649aLong12/28/2021
166
27FALSEacscatal.0c0399310.1021/acscatal.0c03993https://sci-hub.wf/10.1021/acscatal.0c03993https://doi.org/10.1021/acscatal.0c03993NiC-O ActivationShihongTRUE25132020Lian, Z
Nickel-Catalyzed Cross-Electrophile Coupling Reactions for the Synthesis of gem-Difluorovinyl ArenesACS CATALYSIS
A nickel-catalyzed cross-electrophile coupling reaction between (hetero)aryl bromides and 2,2-difluorovinyl tosylate is presented. This protocol provides facile incorporation of the gem-difluorovinyl moiety in organic molecules. The method features mild reaction conditions, good functional group tolerance, and excellent yields. Furthermore, mechanistic experiments and DFT studies indicate a Ni(0)/Ni(II) catalytic cycle, thus differing from the currently accepted catalytic cycle for nickel-catalyzed C(sp(2))-C(sp(2)) cross-electrophile coupling reactions.
Sichuan Univ11/20/2020TRUETRUEFALSECsp2-Csp2_arE-EOXOTfBrVinylArylNo baseNo BaseWeak0.53_xxx10.1021/acscatal.1c0480010.1002/adsc.202101388,10.6023/cjoc202108006,10.1021/acs.orglett.1c04018,10.1021/acscatal.1c04800,10.1039/d1qo01406d,10.1021/acs.orglett.1c03329,10.1021/acs.orglett.1c03305,10.1039/d1qo01460a,10.1021/acscatal.1c02307,10.1021/acscatal.1c02952,10.1021/acs.joc.1c01724,10.1055/a-1608-5693,10.1039/d1gc01983j,10.1039/d1qo00549a,10.1021/jacs.1c03126,10.1055/s-0040-1720474,10.1039/d1cc01132d,10.1039/d0qo01630f11/5/2021NOV 202020FALSEFALSEFALSEFALSE102213616
167
10FALSEacscatal.1c0301010.1021/acscatal.1c03010https://sci-hub.wf/10.1021/acscatal.1c03010https://doi.org/10.1021/acscatal.1c03010NiC-O ActivationKellyTRUE31382021
Stradiotto, M
CgPhen-DalPhos Enables the Nickel-Catalyzed O-Arylation of Tertiary Alcohols with (Hetero)Aryl ElectrophilesACS CATALYSIS
While the Ni-catalyzed cross-coupling of primary or secondary aliphatic alcohols and (hetero)aryl electrophiles is known, related cross-couplings involving tertiary aliphatic alcohols, with a broad scope, are challenging. Herein we disclose that a NiII precatalyst featuring the ligand CgPhen-DalPhos is unusual in its ability to promote the C-O cross-coupling of tertiary aliphatic alcohols with (hetero)aryl halides (Cl, Br, and I) or phenol derivatives (OMs and OPiv). An exploration of substrate scope and competition experiments help to shed light on the capabilities and reactivity preferences of this catalyst system.
Dalhousie Univ9/3/2021Csp2_ar-Osp2E-NuOHOMsHArylORIonic-OtBuWeak0.36_x10.1021/acscatal.1c0520810.1021/acscatal.1c04895,10.1039/d1sc06968c1/16/2022
168
251FALSEacscatal.1c0480010.1021/acscatal.1c04800https://sci-hub.wf/10.1021/acscatal.1c04800https://doi.org/10.1021/acscatal.1c04800NiC-O ActivationLongTRUE11312021Mazet, C
Nickel-Catalyzed Kumada Vinylation of Enol Phosphates: A Comparative Mechanistic StudyACS CATALYSIS
Based on supporting stoichiometric organometallic syntheses, structural analyses, reaction monitoring, radical-clock experiments, and kinetic investigations, a comparative mechanistic study between two related systems that are competent in the Ni-catalyzed Kumada cross-coupling reaction between enol phosphates and vinyl magnesium bromide is reported. We demonstrate that the two bisphosphine-nickel complexes operate via Ni(0)/Ni(II) catalytic manifolds for this type of C(sp(2))-O electrophiles. The first complex of generic structure [(dppe)NiBr2] is reduced in situ upstream from the productive catalytic cycle, which itself follows a classical mechanistic scenario composed of an oxidative addition/transmetalation/reductive elimination sequence. A rapid phosphate/bromide ion exchange prior to transmetalation constitutes a key feature of this system. The related [(dmpe)NiBr2] complex follows a much less conventional pathway. Kinetic analyses distinguish themselves by an unusual apparent second order in the catalyst, which is attributed to an interplay between vinyl nickel species formed during precatalyst activation and styrenyl nickel intermediates generated downstream in the sequence of elementary steps. This hypothesis is corroborated by independent supporting organometallic investigations.
#N/A12/17/2021Csp2-Csp2E-NuOMg
OP(O)(OEt)2
MgX
Carbonyl
VinylNo baseNo BaseStrong0.04_10.1002/anie.202110785,10.1021/jacs.1c06553,10.1021/acs.oprd.1c00053,10.1021/acscatal.1c01626,10.1055/a-1509-5954,10.1039/d1sc00822f,10.1021/acs.organomet.0c00775,10.1021/acscatal.0c03993,10.1021/acscatal.0c02514,10.1055/s-0040-1707900,10.1021/acscatal.0c02115,10.1021/acs.accounts.0c00032,10.1016/j.trechm.2019.08.004,10.1038/s41557-019-0319-5,10.1021/acs.organomet.9b00543,10.1021/acscatal.9b00744,10.1039/c8ob01895b,10.1039/c8sc04698k,10.1038/s41586-018-0669-y,10.1021/jacs.8b09849,10.1021/acs.organomet.8b00350,10.1021/jacs.8b04479,10.1038/s41467-018-03928-z,10.1021/acscatal.8b00546,10.1039/C7SC04675H,10.1021/acscatal.7b04030,10.1021/jacs.7b10537,10.1021/acscatal.7b00616,10.1021/acscatal.7b02919,10.1021/jacs.7b04279,10.1021/acs.organomet.7b00208,10.1038/s41570-017-0025,10.1039/c6sc02895k,10.1021/jacs.6b10998,10.1021/jacs.6b11412,10.1002/anie.201609757,10.1021/acs.organomet.6b00371,10.1021/acscatal.6b00801,10.1021/jacs.6b03253,10.1002/anie.201505699,10.1016/j.ica.2015.07.030,10.1021/acs.accounts.5b00242,10.1038/ncomms8508,10.1021/acs.accounts.5b00051,10.1021/acscatal.5b00072,10.1039/c5dt01040c,10.1038/nature13274,10.1021/ol403209k,10.1039/c4cs00206g,10.1021/ic401296f,10.1021/ja311940s,10.1039/c3ra44884c,10.1021/ol301847m,10.1021/ja210249h,10.1021/ic2007342,10.1021/cr100259t,10.1021/cr100327p,10.1002/chem.201002273,10.1039/b922984a,10.1039/b809676g,10.2174/138527207782418744,10.1002/anie.200453765,10.1002/(SICI)1521-3773(19990712)38:13/14<1985::AID-ANIE1985>3.0.CO;2-7,10.1039/a804198i,10.1038/32623,10.1021/ja970619+,10.1021/jo00126a047,10.1021/jo00041a004,10.1515/znb-1991-1018,10.1021/jo00207a044checked by Kelly12/29/2021
169
11FALSEacscatal.1c0520810.1021/acscatal.1c05208https://sci-hub.wf/10.1021/acscatal.1c05208https://doi.org/10.1021/acscatal.1c05208NiC-O ActivationGerryTRUE111382022Weix, DJ
In-Situ Bromination Enables Formal Cross-Electrophile Coupling of Alcohols with Aryl and Alkenyl HalidesACS CATALYSIS
Although alcohols are one of the largest pools of alkyl substrates, approaches to utilize them in cross-coupling and cross-electrophile coupling are limited. We report the use of 1 degrees and 2 degrees alcohols in cross-electrophile coupling with aryl and vinyl halides to form C(sp(3))-C(sp(2)) bonds in a one-pot strategy utilizing a very fast (<1 min) bromination. The reaction's simple benchtop setup and broad scope (42 examples, 56% +/- 15% average yield) facilitates use at all scales. The potential in parallel synthesis applications was demonstrated by successfully coupling all combinations of 8 alcohols with 12 aryl cores in a 96-well plate.
Univ Wisconsin1/7/2022Csp3-Csp2_arE-EOXOHBrAlkylArylBarton's base#N/A#N/AStrong-0.81_xxx10.1021/jacs.1c122031/10/2022
170
180FALSEacs.orglett.6b0223610.1021/acs.orglett.6b02236https://sci-hub.wf/10.1021/acs.orglett.6b02236https://doi.org/10.1021/acs.orglett.6b02236NiC-H ActivationGerryTRUE551#N/A2016Shi, BF
Nickel-Catalyzed Ortho-Arylation of Unactivated (Hetero)aryl C-H Bonds with Arylsilanes Using a Removable AuxiliaryORG LETT
Ni(II)-catalyzed ortho-arylation of aromatic and heteroaromatic carboxamides with triethoxy(aryl)silanes assisted by a removable bidentate auxiliary is reported. This transformation features a broad substrate scope, good functional group tolerance, and compatibility with heterocyclic substrates. Compared to the well-established Ni(II)-catalyzed C-H arylation with ArX or aryliodonium salts via oxidative addition, this reaction proceeded via a fluoride-promoted transmetalation.
Zhejiang Univ9/16/2016yCsp2_ar-Csp2_arE-NuSiH
(OEt)3-Si
HArylArylNa2CO3Ionic-CO3_xx10.1021/acscatal.7b0104410.1021/acsomega.1c02481,10.1039/d0ob02301a,10.1021/acs.joc.0c02631,10.1021/acs.orglett.0c03578,10.1016/j.tetlet.2020.152612,10.1016/j.tetlet.2020.152553,10.1002/ajoc.202000529,10.1039/d0ob01212b,10.1002/cjoc.201900468,10.1039/c9qo01497g,10.1021/acs.orglett.0c00631,10.3762/bjoc.16.26,10.1021/acs.chemrev.9b00495,10.1002/adsc.201901158,10.1021/jacs.9b09109,10.1021/acs.orglett.9b02145,10.1055/s-0037-1611799,10.1039/c9nj02191d,10.1016/j.trechm.2019.06.002,10.1002/ajoc.201900362,10.1002/cjoc.201900090,10.1016/j.apcata.2019.04.020,10.1039/c9cy00009g,10.1039/c8qo01274a,10.1002/ejoc.201900067,10.1021/acs.chemrev.8b00507,10.1002/chem.201806114,10.1016/j.tet.2018.11.051,10.1002/adsc.201800923,10.1021/acscatal.8b03770,10.1039/c8cc07481j,10.1039/c8cs00201k,10.1055/s-0037-1609558,10.1002/adsc.201800216,10.1038/NCHEM.2900,10.1021/acs.orglett.7b03567,10.6023/cjoc201703036,10.1039/c7cc05532c,10.1039/c7ob01353a,10.1039/c7cc05011a,10.1002/ajoc.201700110,10.1021/acscatal.7b01683,10.1039/c7ob00818j,10.1021/acs.joc.7b00659,10.1021/acscatal.7b01044,10.1002/cssc.201700321,10.1021/acs.joc.7b00256,10.1039/c7sc00156h,10.1021/acs.joc.7b00002,10.1021/acs.orglett.6b03746,10.1039/c6qo00589f,10.1039/c6cc08408g,10.1021/acs.joc.6b0242312/29/2021
171
304FALSEacscatal.2c0051210.1021/acscatal.2c00512https://sci-hub.wf/10.1021/acscatal.2c00512https://doi.org/10.1021/acscatal.2c00512NiC-O ActivationxWilliam12-JunTRUE01#N/A2022Renaud, JL
Dual Ni/Organophotoredox Catalyzed Allylative Ring Opening Reaction of Oxabenzonorbornadienes and AnalogsACS CATALYSIS
A general approach for the allylation of oxa- and azabenzonorbornadienes is reported by merging organophotoredox and nickel catalysis. This methodology allowed the diastereoselective allylation of various heterocyclic alkene derivatives with a broader range of allylic acetate compounds compared to previously published procedures. Moreover, no air-sensitive organometallic species and no metal reductants (such as zinc or manganese) are required for the ring opening. Mechanistic studies suggest that the ring opening proceeds through a carbometalation process.
3/18/2022Csp3-Csp3E-EOO
O(Ring-Opening)
OAcAlkylAllylEt3NNitrogenNitrogen(neutral)Weak16/16/2022
172
182FALSEs41467-019-11392-610.1038/s41467-019-11392-6https://sci-hub.wf/10.1038/s41467-019-11392-6https://doi.org/10.1038/s41467-019-11392-6NiC-H ActivationLongTRUE721#N/A2019Lu, Z
Enantioselective benzylic C-H arylation via photoredox and nickel dual catalysisNAT COMMUN
The asymmetric cross-coupling reaction is developed as a straightforward strategy toward 1,1-diaryl alkanes, which are a key skeleton in a series of natural products and bioactive molecules in recent years. Here we report an enantioselective benzylic C(sp(3))-H bond arylation via photoredox/nickel dual catalysis. Sterically hindered chiral biimidazoline ligands are designed for this asymmetric cross-coupling reaction. Readily available alkyl benzenes and aryl bromides with various functional groups tolerance can be easily and directly transferred to useful chiral 1,1-diaryl alkanes including pharmaceutical intermediates and bioactive molecules. This reaction proceeds smoothly under mild conditions without the use of external redox reagents.
Zhejiang Univ8/7/2019Csp3-ring(s)-Csp2_arE-EXXBrBrBenzylArylNo baseNo Base_10.1039/d1sc07237d,10.1039/d1cs00727k,10.1038/s41467-021-27507-x,10.1002/cjoc.202100819,10.1039/d1qo01689j,10.1039/d1cc06285a,10.1038/s41467-021-26794-8,10.1002/anie.202110233,10.6023/A21070345,10.6023/cjoc202107044,10.1039/d1ob01774h,10.1039/d1qo01421h,10.1055/a-1677-5870,10.1021/acscatal.1c04314,10.1039/d1cs00210d,10.1021/jacs.1c08105,10.1021/acs.orglett.1c02725,10.1021/acs.joc.1c01621,10.3762/bjoc.17.143,10.1021/acscatal.1c02851,10.3762/bjoc.17.126,10.1039/d1gc00993a,10.1038/s41467-021-23887-2,10.1039/d1cc01756j,10.1021/acsami.1c03098,10.1055/s-0040-1720406,10.1038/s41467-021-22690-3,10.1039/d0sc06666d,10.1021/acs.joc.0c02556,10.1002/cjoc.202000486,10.1038/s41467-020-20888-5,10.1038/s41467-020-20770-4,10.1007/s11426-020-9910-2,10.1016/j.cjche.2020.05.023,10.1055/a-1344-2473,10.1021/jacs.0c08823,10.1021/jacs.0c10471,10.1039/d0ob01652g,10.1002/anie.202011342,10.1039/d0sc01445a,10.1055/s-0040-1707301,10.3762/bjoc.16.197,10.1002/anie.202010386,10.1002/anie.202007668,10.1016/j.chempr.2020.04.022,10.1039/d0qo00587h,10.1039/d0cc01480j,10.1021/acscatal.0c00871,10.1021/acscatal.0c00610,10.1039/d0ra02673e,10.1021/acs.orglett.0c00293,10.1007/s11426-019-9711-x,10.1007/s11426-019-9701-5,10.1002/ejoc.202000144,10.1021/acscatal.9b05598,10.1021/jacs.9b13920,10.1038/s41467-020-14459-x,10.1016/j.isci.2019.11.008,10.1021/acs.orglett.9b033381/6/2022
173
162FALSEacscatal.5b0049810.1021/acscatal.5b00498https://sci-hub.wf/10.1021/acscatal.5b00498https://doi.org/10.1021/acscatal.5b00498NiC-O ActivationShihongTRUE834122015Monfette, S
Dual Ni/Organophotoredox Catalyzed Allylative Ring Opening Reaction of Oxabenzonorbornadienes and AnalogsACS CATALYSIS
A general approach for the allylation of oxa-and azabenzonorbornadienes is reported by merging organophotoredox and nickel catalysis. This methodology allowed the diastereoselective allylation of various heterocyclic alkene derivatives with a broader range of allylic acetate compounds compared to previously published procedures. Moreover, no air-sensitive organometallic species and no metal reductants (such as zinc or manganese) are required for the ring opening. Mechanistic studies suggest that the ring opening proceeds through a carbometalation process.
Pfizer Inc5/1/2015TRUEFALSEFALSECsp2_ar-Csp2_arE-NuOBOBocB(nep)ArylArylK3PO4Ionic-PO4Medium0.31_10.1021/acs.orglett.6b01398,10.1002/anie.201805611,10.1002/chem.201605095,10.1021/jacs.6b1141210.1039/d1ra04572e,10.1021/acs.joc.1c00577,10.1021/acs.oprd.1c00053,10.1016/j.cej.2021.130342,10.6023/cjoc202009029,10.1039/d1qo00309g,10.1002/tcr.202000148,10.2174/1570193X17999200723160453,10.1055/s-0040-1705972,10.1021/acs.organomet.0c00485,10.1021/acsomega.0c03415,10.1039/d0nj01610a,10.1039/d0dt02063j,10.1021/acs.chemrev.9b00682,10.1021/acs.oprd.0c00104,10.1039/d0ob00244e,10.1021/acsomega.9b04450,10.1002/anie.202000124,10.1002/ejoc.201901851,10.1021/acs.orglett.9b03434,10.1038/s41929-019-0407-3,10.1038/s41929-019-0392-6,10.1016/j.tetlet.2019.151148,10.1039/c9cy00752k,10.1021/acs.jchemed.8b00945,10.1002/anie.201906148,10.1002/pola.29426,10.1039/c9sc00554d,10.1039/c9ob00561g,10.1002/chem.201900276,10.1021/acs.orglett.9b00946,10.1007/s00706-019-2364-6,10.1021/acs.chemrev.8b00361,10.1021/acs.inorgchem.8b02991,10.1039/c8nj05503c,10.1021/acs.organomet.8b00589,10.1021/acs.jpcc.8b07538,10.1021/acs.organomet.8b00351,10.1002/anie.201805611,10.1002/cctc.201800454,10.1021/acscatal.8b02187,10.1021/acscatal.8b00933,10.3390/molecules23061449,10.1021/acscatal.8b01005,10.1002/chem.201801241,10.6023/cjoc201709041,10.1021/acscatal.8b00230,10.1038/s41557-018-0021-z,10.1039/c8cc00271a,10.1055/s-0036-1591853,10.2174/1385272822666180704143509,10.1016/bs.aihch.2017.10.001,10.1055/s-0036-1589101,10.1021/acs.orglett.7b02823,10.1002/anie.201707906,10.1021/acsomega.7b01159,10.1002/anie.201704948,10.1055/s-0036-1588806,10.1002/ejoc.201700660,10.1021/acs.organomet.7b00129,10.1038/s41570-017-0025,10.1021/acs.organomet.6b00885,10.1021/jacs.6b11412,10.1002/chem.201605095,10.1016/j.poly.2016.05.037,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1021/acs.chemrev.6b00193,10.1021/acs.organomet.6b00485,10.1021/acs.orglett.6b01758,10.1002/tcr.201500305,10.1021/acs.oprd.6b00229,10.1002/ejic.201600181,10.1021/acs.orglett.6b01398,10.1021/acs.organomet.6b00256,10.1021/acscatal.5b02718,10.1039/c6sc01457g,10.1039/c6ra01918h,10.1002/chem.201504049,10.1021/acs.oprd.5b00314,10.1002/anie.201505136,10.1021/acs.oprd.5b00302Kelly11/16/2021MAY2015FALSEFALSEFALSEFALSE553120
174
119FALSEacscatal.5b0102110.1021/acscatal.5b01021https://sci-hub.wf/10.1021/acscatal.5b01021https://doi.org/10.1021/acscatal.5b01021NiC-O ActivationGerryTRUE635102015Hanley, PS
Development of an Air-Stable, Broadly Applicable Nickel Source for Nickel-Catalyzed Cross-CouplingACS CATALYSIS
The synthesis of NiCl(o-tolyl)(TMEDA) (3; TMEDA = tetramethylethylenediamine) and its application in coupling reactions is described. In combination with a suitable ligand, precatalyst 3 was applied to a wide range of transformations, such as Suzuki, amination, Kumada, Negishi, Heck, borylation, and reductive coupling. Yields of products obtained with 3 are equal or superior to those obtained with common Ni sources such as Ni(cod)(2) (1) and NiCl2(dme) (2). Importantly, and unlike 1, complex 3 is stable for months in air as a solid, which eliminates the need for a glovebox and greatly facilitates the reaction setup. Thus, complex 3 is the first highly versatile Ni source that combines the broad applicability of 1 with the air stability of 2.
Dow Chem Co USA9/1/2015TRUETRUETRUECsp2_ar-Csp2_arE-NuOBOFsB(OH)2ArylArylK3PO4Ionic-PO4Weak0.53TMxxx10.1021/jacs.6b11412,10.1021/acscatal.6b00865,10.1021/jacs.0c06995,10.1021/acs.joc.8b02498,10.1021/acscatal.9b0074410.1039/d1sc05316g,10.1080/00397911.2021.1955931,10.1073/pnas.2103513118,10.1039/d1cc02617h,10.1021/acs.orglett.1c01734,10.1021/acscatal.1c01201,10.1055/a-1503-6330,10.1039/d1cc00769f,10.1021/acs.orglett.1c00671,10.1002/ejoc.202001485,10.1021/jacs.0c06995,10.1039/d0cy01159b,10.1021/acs.orglett.0c02566,10.1039/d0ob00406e,10.1002/chem.202000721,10.2174/1385272824666200211114540,10.1002/anie.201911465,10.1021/acs.joc.9b02394,10.1021/acs.joc.9b02352,10.1016/j.molstruc.2019.07.054,10.1039/c9sc03570b,10.1016/j.jorganchem.2019.120937,10.1039/c9qo00747d,10.1002/advs.201901551,10.1073/pnas.1909972116,10.1039/c8cs00960k,10.1039/c9cc02659b,10.1039/c9ob00903e,10.1021/acs.orglett.9b00836,10.1021/acscatal.9b00744,10.1002/ejoc.201801825,10.1002/chem.201805175,10.1016/j.poly.2018.11.044,10.1021/acs.joc.8b02785,10.1016/j.catcom.2018.08.023,10.1002/slct.201802120,10.1039/c8qo00729b,10.1021/acs.joc.8b02498,10.3390/molecules23102435,10.1021/acs.joc.8b01762,10.1039/c8qo00295a,10.1021/acscatal.8b00856,10.1002/ajoc.201700591,10.1002/ajoc.201800037,10.1002/anie.201712429,10.1002/anie.201712145,10.1021/acs.orglett.7b03950,10.1021/acs.orglett.7b02522,10.1002/asia.201700891,10.1002/ajoc.201700064,10.1016/j.tetlet.2017.04.070,10.1021/acs.joc.7b00481,10.1021/jacs.6b12911,10.1021/jacs.6b11412,10.1002/chem.201602926,10.1021/acscatal.6b00865,10.1002/chem.201600167,10.1021/acs.joc.5b02667,10.1021/acs.joc.5b02770Kelly11/4/2021SEP2015FALSEFALSEFALSEFALSE595041
175
136FALSEacscatal.6b0080110.1021/acscatal.6b00801https://sci-hub.wf/10.1021/acscatal.6b00801https://doi.org/10.1021/acscatal.6b00801NiC-O ActivationKellyTRUE7016892016Rueping, M
Nickel- and Palladium-Catalyzed Coupling of Aryl Fluorosulfonates with Aryl Boronic Acids Enabled by Sulfuryl FluorideACS CATALYSIS
Herein are reported examples of the nickel- and palladium-catalyzed cross-coupling of aryl fluorosulfonates and aryl boronic acids. These reactions occur in good to excellent yields under mild conditions with excellent functional group compatibility employing either Pd(OAc)(2) and inexpensive PPh3 or the inexpensive and readily available NiCl2(PCy3)(2). Importantly, the in situ conversion of phenol derivatives to the corresponding aryl fluorosulfonate by reaction with sulfuryl fluoride and a base and subsequent cross-coupling to form biaryls in a single pot are described. The combination of inexpensive sulfuryl fluoride and efficient catalysts reported in these methodologies will enable economical Suzuki coupling of phenols in pharmaceutical and agrochemical processes.
Rhein Westfal TH Aachen
7/1/2016TRUETRUEFALSECsp2_ar-Csp3E-NuOB
OCONEt2
9-BBNArylAlkylCs2CO3Ionic-CO3Medium0.31_xx10.1021/jacs.7b12865,10.1021/acs.joc.6b01627,10.1021/acscatal.1c04800,10.1021/jacs.7b04973,10.1002/anie.202103327,10.1039/c9sc00783k,10.1002/chem.201702867,10.1021/jacs.1c09797,10.1002/anie.202004116,10.1039/c6cc09685a,10.1021/acs.orglett.7b00556,10.1021/acscatal.7b01058,10.1021/acs.orglett.8b01021,10.1039/c7cc06717h,10.1002/anie.201607646,10.1021/acscatal.7b0094110.1021/acscatal.1c04800,10.1021/jacs.1c09797,10.1002/adsc.202100585,10.1039/d1ob00955a,10.1039/d1nj02677a,10.1021/acs.organomet.1c00085,10.1002/anie.202103327,10.1002/cjoc.202000319,10.1021/acs.joc.0c01732,10.1021/acs.chemrev.0c00088,10.1021/acs.orglett.0c02609,10.1002/anie.202004116,10.1039/d0sc01641a,10.1002/cjoc.201900506,10.3390/catal10030296,10.1002/chem.201904842,10.1021/acs.organomet.9b00197,10.1016/j.jcat.2019.07.026,10.1039/c9nj01748h,10.1039/c9ra02394a,10.1039/c9sc00783k,10.1021/acs.orglett.9b00946,10.1039/c8ob02977f,10.6023/cjoc201809027,10.1007/3418_2018_19,10.1016/j.tetlet.2018.11.038,10.1016/j.tet.2018.10.025,10.1021/acs.orglett.8b02351,10.1002/adsc.201800729,10.1016/j.jallcom.2018.03.356,10.1039/c8ob01034j,10.1021/acs.orglett.8b01646,10.3390/molecules23071715,10.1002/chem.201704670,10.1016/j.jorganchem.2018.01.019,10.1021/acs.orglett.8b01021,10.1021/acs.accounts.8b00023,10.1021/jacs.7b12865,10.1021/acs.orglett.7b03713,10.1002/ejoc.201701142,10.1021/acs.orglett.7b03669,10.1039/c8ra05311a,10.1039/c8ra04984j,10.1039/c7cc06717h,10.1055/s-0036-1591495,10.1002/anie.201706597,10.1021/jacs.7b04973,10.1002/chem.201702867,10.1021/acs.orglett.7b01905,10.1021/acscatal.7b00941,10.1021/acscatal.7b01058,10.1002/ejoc.201700514,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1002/anie.201612624,10.1021/acs.orglett.6b03861,10.1002/anie.201611720,10.1039/c6cc09685a,10.1021/acscatal.6b02964,10.1002/anie.201607646,10.1002/chem.201604452,10.1002/chem.201604504,10.1246/cl.160712,10.1021/acs.joc.6b01627,10.1002/anie.201604696,10.1016/bs.adomc.2016.07.001Kelly11/1/2021JUL2016FALSEFALSEFALSEFALSE674438
176
186FALSEacs.orglett.9b0101610.1021/acs.orglett.9b01016https://sci-hub.wf/10.1021/acs.orglett.9b01016https://doi.org/10.1021/acs.orglett.9b01016NiC-N ActivationTRUE674182019Martin, R
Ni-catalyzed Reductive Deaminative Arylation at sp(3) Carbon CentersORG LETT
A Ni-catalyzed reductive deaminative arylation at unactivated sp(3) carbon centers is described. This operationally simple and user-friendly protocol exhibits excellent chemoselectivity profile and broad substrate scope, thus complementing existing metal-catalyzed cross-coupling reactions to forge sp(3) C-C linkages. These virtues have been assessed in the context of late-stage functionalization, hence providing a strategic advantage to reliably generate structure diversity with amine-containing drugs.
Barcelona Inst Sci & Technol
4/19/2019TRUETRUEFALSECsp3-Csp2_arE-EXXClBrAlkylHetNo baseNo Base_xxxAdded by YIzhou10.1038/s41467-021-25222-1,10.1002/anie.202002271,10.1021/acs.orglett.9b04497,10.1021/jacs.0c1309310.1021/acs.orglett.2c00317,10.1055/s-0040-1719881,10.1039/d1cs01084k,10.1021/jacs.1c12350,10.1055/s-0041-1737762,10.1021/jacs.1c12622,10.1021/acscatal.1c05329,10.1021/acs.orglett.1c03870,10.1021/jacs.1c10932,10.1021/acs.joc.1c01867,10.1038/s41467-021-27060-7,10.1002/adsc.202100940,10.1021/acs.orglett.1c02708,10.1002/ajoc.202100438,10.1021/acs.orglett.1c02458,10.1038/s41467-021-25222-1,10.1021/acs.orglett.1c01959,10.1039/c9cs00571d,10.1021/acscatal.1c01860,10.1021/acscatal.1c01416,10.1016/j.tetlet.2021.153071,10.1039/d1sc00943e,10.1039/d1sc00986a,10.1039/d1cc00039j,10.1039/d0cs01107j,10.1021/acs.orglett.1c00178,10.1021/jacs.0c13093,10.1039/d0qo01479f,10.1039/d0cc07632e,10.1039/d0ob01807d,10.1021/jacs.0c11172,10.1039/d0cc05725h,10.1021/acs.orglett.0c03347,10.1021/acscatal.0c03237,10.1021/acs.accounts.0c00291,10.1039/d0cc04062b,10.1021/acscatal.0c01842,10.1021/acs.orglett.0c01592,10.1002/anie.202006048,10.1002/adsc.202000457,10.1002/anie.202002271,10.1002/anie.201914555,10.1021/jacs.0c01724,10.3762/bjoc.16.74,10.1002/anie.201911660,10.1039/d0sc00225a,10.1002/chem.202000412,10.1021/acs.orglett.9b04497,10.1002/anie.201916279,10.1055/s-0039-1690703,10.1039/c9cc08348k,10.1002/aoc.5379,10.1039/c9cc08333b,10.1002/chem.201905048,10.1002/asia.201901490,10.1021/acs.orglett.9b03899,10.1021/acs.orglett.9b03284,10.1021/jacs.9b07489,10.1002/adsc.201901011,10.1021/acscatal.9b03084,10.1021/acs.orglett.9b02643,10.1021/acs.orglett.9b02534,10.1038/s41929-019-0292-9Long11/16/2021
177
107FALSEacscatal.6b0086510.1021/acscatal.6b00865https://sci-hub.wf/10.1021/acscatal.6b00865https://doi.org/10.1021/acscatal.6b00865NiC-O ActivationLongTRUE582102016Hanley, PS
Nickel-Catalyzed C-sp2-C-sp3 Cross-Coupling via C-O Bond ActivationACS CATALYSIS
A new and efficient nickel-catalyzed alkylation of C-Ar-O electrophiles with B-alkyl-9-BBNs is described. The transformation is characterized by its functional group tolerance and provides a practical and versatile access to various C-sp2-C-sp3 bonds through C-sp2-O substitution, without the restriction of beta-hydride elimination. Moreover, the advantage of the newly developed method was demonstrated in a selective and sequential C-O bond activation process.
Dow Chem Co USA6/1/2016TRUEFALSEFALSECsp2_ar-Nsp3E-NuOHOFsHAryl
N(H)Aryl
Ionic-OtBuWeak0.53_x10.1021/acs.joc.8b02498,10.1021/acs.orglett.7b0055610.1016/j.tet.2022.132657,10.1002/slct.202104114,10.1039/d1sc05316g,10.1070/RCR4999,10.1080/00397911.2021.1955931,10.1039/d1cc02617h,10.1055/a-1524-4912,10.1039/d1cc00769f,10.1002/ejoc.202001485,10.1039/d0cy01159b,10.1039/d0nj01610a,10.1002/chem.202001685,10.1002/slct.202002270,10.1021/acs.chemrev.9b00682,10.1039/d0ra04629a,10.1039/d0ra02631j,10.1002/anie.201911465,10.1021/acs.joc.9b02394,10.1021/acs.joc.9b02352,10.1021/acs.orglett.9b03274,10.1039/c9qo00747d,10.1002/advs.201901551,10.1039/c9ra05346h,10.1002/anie.201904795,10.1039/c9ob01547g,10.1016/j.tet.2019.07.007,10.3762/bjoc.15.186,10.1002/ejoc.201900844,10.1055/s-0037-1611840,10.1002/ejoc.201900478,10.1021/acs.joc.9b00703,10.1039/c9ob00699k,10.1002/ejoc.201801888,10.1021/acs.joc.8b02785,10.1016/j.catcom.2018.08.023,10.1021/acs.joc.8b02498,10.1002/asia.201800575,10.1039/c8dt01852a,10.3390/molecules23071715,10.1039/c8qo00295a,10.1039/c8cy00129d,10.1002/ajoc.201700591,10.1002/anie.201712429,10.1021/acs.orglett.7b03950,10.1021/acs.orglett.7b02522,10.1039/c7ob01791j,10.1002/asia.201700891,10.1002/ajoc.201700064,10.1055/s-0036-1588806,10.1002/ejoc.201700585,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1021/acs.organomet.6b00885,10.1021/jacs.6b12911Kelly10/31/2021JUN2016FALSEFALSEFALSEFALSE663515
178
289FALSEacscatal.7b0077210.1021/acscatal.7b00772https://sci-hub.wf/10.1021/acscatal.7b00772https://doi.org/10.1021/acscatal.7b00772NiC-O ActivationxWilliam29-MayTRUE551852017Molander, GA
Palladium- and Nickel-Catalyzed Amination of Aryl FluorosulfonatesACS CATALYSIS
Examples of the palladium- and nickel-catalyzed amination of aryl fluorosulfonates with aromatic and alkyl amines are described. Aniline is coupled to a diverse series of aryl fluorosulfonates catalyzed by the combination of CpPd(cinammyl) and Xantphos, and the relative reactivity of aryl fluorosulfonates to undergo Pd-catalyzed amination was compared with other common aryl electrophiles. In addition, we report the direct amination of a phenol by in situ formation of an aryl fluorosulfonate by reaction with sulfuryl fluoride and base followed by subsequent amination to form a new C-N bond. Finally, we report examples of the nickel-catalyzed amination of aryl fluorosulfonates catalyzed by the combination of Ni(COD)(2) and DPPF in the presence of MeCN. The high reactivity of the aryl fluorosulfonate electrophile with generic palladium and nickel catalyst systems, combined with its simple preparation from sulfuryl fluoride will enable commercial amination reactions of abundant phenolic raw materials.
1/6/2017Csp3-ring(s)-Csp2_arE-EOX
OC(S)SMe
BrBenzylArylNo baseNo BaseMedium 6/15/2022
179
143FALSEacscatal.7b0094110.1021/acscatal.7b00941https://sci-hub.wf/10.1021/acscatal.7b00941https://doi.org/10.1021/acscatal.7b00941NiC-O ActivationShihongTRUE755892017Rueping, M
O-Benzyl Xanthate Esters under Ni/Photoredox Dual Catalysis: Selective Radical Generation and Csp(3)-Csp(2) Cross-CouplingACS CATALYSIS
Alkyl xanthate esters are perhaps best known for their use in deoxygenation chemistry. However, their use in cross-coupling chemistry has not been productive, which is due, in part, to inadequate xanthate activation strategies. Herein, we report the use of O-benzyl xanthate esters, readily derived from alcohols, as radical pronucleophiles in Csp(3)-Csp(2) cross couplings under Ni/photoredox dual catalysis. Xanthate (C-O) cleavage is found to be reliant on photogenerated (sec-butyl) radical for nickel-catalyzed cross-couplings. Mechanistic experiments support independently, and relative rates are carefully orchestrated, such that no activators to form new carbon-centered radicals primed the fact that the key radical components are formed cross reactivity is observed.
Rhein Westfal TH Aachen
7/1/2017TRUETRUEFALSECsp2_ar-Csp3E-NuOZnOPivZnXArylAlkylNo baseNo BaseMedium0.33_x10.1021/jacs.7b12865,10.1002/chem.201702867,10.1021/acscatal.9b00884,10.1021/acs.orglett.8b01021,10.1021/jacs.8b0213410.1039/d1qo01756j,10.1039/d1sc06968c,10.1021/acs.organomet.1c00578,10.1039/d1gc03724b,10.1002/adsc.202101241,10.1039/d1ob00955a,10.1002/anie.202106356,10.1002/anie.202103465,10.1021/acs.organomet.1c00085,10.1039/d0cc08389e,10.1002/cctc.202001949,10.1021/acs.chemrev.0c00153,10.1021/acs.orglett.0c03342,10.1002/cjoc.202000319,10.1055/s-0040-1705943,10.1021/acs.chemrev.0c00088,10.1021/acs.chemrev.9b00682,10.1039/d0ob00789g,10.1021/jacs.0c02839,10.1002/adsc.202000122,10.1021/acs.orglett.0c00542,10.1002/asia.202000117,10.1039/c9qo01428d,10.3390/catal10020230,10.1039/c9cc07558e,10.1002/chem.201904842,10.1021/acs.joc.9b02323,10.1021/jacs.9b08586,10.1002/anie.201911372,10.1021/acs.orglett.9b03170,10.1002/aoc.5181,10.1039/c9nj01748h,10.1021/acscatal.9b00884,10.1021/acs.orglett.9b00774,10.1021/acs.joc.8b03114,10.1038/s41467-018-08063-3,10.1007/3418_2018_19,10.1002/anie.201811139,10.3390/molecules23102412,10.1021/acsomega.8b02155,10.1002/asia.201800478,10.1002/adsc.201800729,10.1002/anie.201805486,10.1039/c8dt01857j,10.1021/acs.orglett.8b01646,10.1002/ajoc.201800207,10.1002/chem.201704670,10.1007/s10570-018-1815-2,10.1246/cl.180226,10.1021/acs.orglett.8b01021,10.1021/acs.orglett.8b01233,10.1021/acs.accounts.8b00023,10.1021/acscatal.8b01224,10.1021/acs.organomet.7b00894,10.1021/jacs.8b02134,10.1002/adsc.201701563,10.1021/jacs.7b12865,10.1002/chem.201705842,10.1021/acs.orglett.7b03713,10.1021/acs.orglett.8b00080,10.1039/c7cc08709h,10.1021/acs.orglett.7b03669,10.1021/acs.joc.7b02588,10.1055/s-0036-1591495,10.1055/s-0036-1589120,10.1021/acs.orglett.7b02823,10.1021/acs.organomet.7b00565,10.1002/chem.201702867,10.1021/acs.orglett.7b01905 Long 11/5/2021JUL2017FALSEFALSEFALSEFALSE774491
180
190FALSEsciadv.aaw951610.1126/sciadv.aaw9516https://sci-hub.wf/10.1126/sciadv.aaw9516https://doi.org/10.1126/sciadv.aaw9516NiC-N ActivationElaineTRUE717#N/A2019
Han, JL; Wang, Y; Yan, H
Ni-catalyzed deaminative cross-electrophile coupling of Katritzky salts with halides via C-N bond activationSCI ADV
The reductive cross-coupling of sp(3)-hybridized carbon centers represents great synthetic values and insurmountable challenges. In this work, we report a nickel-catalyzed deaminative cross-electrophile coupling reaction to construct C(sp)-C(sp(3)), C(sp(2))-C(sp(3)), and C(sp(3))-C(sp(3)) bonds. A wide range of coupling partners including aryl iodides, bromoalkynes, or alkyl bromides are stitched with alkylpyridinium salts that derived from the corresponding primary amines. The advantages of this methodology are showcased in the two-step synthesis of the key lactonic moiety of (+)-compactin and (+)-mevinolin. The one-pot procedure without isolation of alkylpyridinium tetrafluoroborate salt is also proven to be successful. This cross-coupling strategy of two electrophiles provides a highly valuable vista for the convenient installation of alkyl substituents and late functionalizations of sp(3) carbons.
Nanjing Univ6/1/2019TRUETRUEFALSECsp3-Csp3E-ENN
Triphenylpyridinium+BF4-
NH2AlkylAlkylNo baseNo Base_xxx10.1038/s41467-021-25222-1,10.1021/acs.orglett.9b04497,10.1021/jacs.0c13093,10.1021/acscatal.1c05208,10.1021/acscatal.1c05208,10.1002/anie.202002271,10.1021/jacs.0c0133010.1021/acs.orglett.2c00317,10.1021/acscatal.1c05738,10.1055/s-0040-1719881,10.1039/d1cs01084k,10.1021/jacs.1c12350,10.1055/s-0041-1737762,10.1021/jacs.1c12622,10.1021/acscatal.1c05208,10.1038/s41467-021-27060-7,10.1002/anie.202112454,10.1039/d1qo01240a,10.1021/acs.orglett.1c03194,10.1021/acs.orglett.1c02708,10.1021/acs.orglett.1c02738,10.1002/ajoc.202100438,10.1021/acs.joc.1c01555,10.1016/j.jorganchem.2021.122042,10.1021/acs.orglett.1c02458,10.1002/anie.202109723,10.1038/s41467-021-25222-1,10.1039/c9cs00571d,10.1021/acscatal.1c01860,10.1039/d1sc01217g,10.1021/acscatal.1c01416,10.1039/d1sc00986a,10.1039/d1cc00039j,10.1021/acs.joc.1c00417,10.1021/jacs.0c13093,10.1039/d0sc06446g,10.1002/ejoc.202001193,10.1021/acssuschemeng.0c08044,10.1039/d0ob01807d,10.1021/acscatal.0c03237,10.1021/acscatal.0c03341,10.1021/acscatal.0c03903,10.1021/jacs.0c08595,10.1038/s41467-020-18834-6,10.1007/s11426-020-9838-x,10.1021/acs.joc.0c01274,10.1021/acs.orglett.0c02105,10.1039/d0nj01294g,10.1021/acs.orglett.0c01592,10.1038/s41467-020-17224-2,10.1021/acs.orglett.0c01488,10.1021/acs.oprd.0c00104,10.1002/anie.202002271,10.1021/acs.organomet.0c00021,10.3762/bjoc.16.74,10.1021/acs.joc.0c00227,10.1002/anie.201911660,10.1002/chem.202000412,10.1021/jacs.0c01330,10.1021/acs.orglett.9b04497,10.1055/s-0039-1690703,10.1039/c9cc07072a,10.1021/acs.orglett.9b03899,10.1021/acs.orglett.9b03284,10.1021/jacs.9b07489,10.1021/acs.orglett.9b02961,10.1021/acscatal.9b03084,10.1021/acs.joc.9b02013,10.1021/acs.orglett.9b02643,10.1021/acs.orglett.9b02534,10.1021/acs.orglett.9b01987Long11/9/2021
181
191FALSEcs501502u10.1021/cs501502uhttps://sci-hub.wf/10.1021/cs501502uhttps://doi.org/10.1021/cs501502uNiC-H ActivationGerryTRUE543722015Hu, XL
Nickel-Catalyzed Direct Alkylation of Terminal Alkynes at Room Temperature: A Hemilabile Pincer Ligand Enhances Catalytic ActivityACS CATAL
Direct coupling of alkyl halides with terminal alkynes provides an efficient and streamlined access to alkyl-substituted alkynes, which are important synthetic intermediates, biologically active molecules, and organic materials. However, until now,there have been fewer than a handful of catalytic methods available for this reaction, and detailed mechanistic studies have not been reported. Herein, we describe the design and development a new nickel pincer complex that catalyzes the direct coupling of primary alkyl halides with terminal alkynes at room temperature. The catalysis has a good substrate scope and high functional group tolerance. Kinetic data suggest that the new pincer ligand is hemilabile, and the dissociation of a labile amine donor is the (t)urnover-determining step of the catalysis. An intermediate Ni-alkynyl species has been isolated and structurally characterized. The reactivity of this species gives insight into the nature of the active species for the activation of alkyl halide.
Ecole Polytech Fed Lausanne
2/1/2015TRUETRUETRUEyCsp1-Csp3E-NuXHXHAlkyneAlkylLiOtBuIonic-OtBu_xxx10.1038/s41467-021-25222-1,10.1021/acs.organomet.6b00201,10.1021/acs.organomet.6b0052910.1055/a-1750-8314,10.1039/d1nj04485k,10.1039/d1qo01217g,10.1038/s41467-021-25222-1,10.1039/d1nj01698a,10.1021/acscatal.1c01542,10.1039/d1ob00280e,10.1039/d0dt03593a,10.1021/acs.organomet.0c00793,10.1002/anie.202100641,10.1039/d0dt03544k,10.1055/s-0040-1705954,10.1016/j.polymer.2020.122860,10.1021/acs.joc.0c01177,10.1039/d0sc01291b,10.1002/anie.202000860,10.1002/adsc.202000189,10.1016/j.ica.2019.119222,10.1002/aoc.5414,10.1038/s41557-019-0346-2,10.1002/adsc.201900603,10.1016/j.ica.2019.118996,10.1021/acs.orglett.9b02190,10.1039/c9qo00335e,10.1002/adsc.201801685,10.1021/acs.accounts.9b00118,10.1039/c8ob02912a,10.1021/acs.inorgchem.8b00958,10.1055/s-0036-1591979,10.1007/s12039-018-1477-5,10.1021/jacs.8b02745,10.1002/anie.201801085,10.1002/adsc.201701556,10.1039/c7cs00693d,10.1021/acs.joc.8b00184,10.1021/acs.orglett.8b00173,10.1021/acs.jpca.7b11713,10.1002/cjoc.201700633,10.1002/adsc.201700798,10.1021/acscatal.7b02615,10.1007/s12039-017-1338-7,10.1021/acs.orglett.7b01194,10.1039/c7cc00891k,10.1021/acs.organomet.6b00529,10.1016/j.molcata.2016.11.007,10.1016/j.tetlet.2016.09.049,10.1021/acscatal.6b01956,10.1007/s41061-016-0067-6,10.1002/anie.201604696,10.1039/c6gc01336h,10.1021/acs.organomet.6b00201,10.1021/acscatal.6b00393,10.1021/acs.orglett.6b00289,10.1016/bs.adomc.2016.08.001,10.1039/c6dt00806b,10.1039/c5sc04232a,10.1021/acscatal.5b02324,10.1055/s-0035-1560374,10.1021/acs.organomet.5b00455,10.1039/c5ra15342e11/22/2021FEB2015FALSEFALSEFALSEFALSE521164
182
192https://sci-hub.wf/https://doi.org/Ni648802016Itami, K#N/ACyanation of Phenol Derivatives with Aminoacetonitriles by Nickel CatalysisORG LETT
Generation of useful arylnitrile structures from simple aromatic feedstock chemicals represents a fundamentally important reaction in chemical synthesis. The first nickel-catalyzed cyanation of phenol derivatives with metal-free cyanating agents, aminoacetonitriles, is described. A nickel-based catalytic system consisting of a unique diphosphine ligand such as dcype or dcypt enables the cyanation of versatile phenol derivatives such as aryl carbamates and aryl pivalates. The use of aminoacetonitriles as a cyanating agent leads to an environmentally and easy-to-use method for arylnitrile synthesis.
Nagoya Univ9/2/2016TRUEFALSEFALSEy_xxxLong added10.1021/acs.joc.8b02498,10.1002/anie.202004116,10.1021/acscatal.7b00941,10.1039/c8sc04437f,10.1021/acs.orglett.7b00556,10.1021/acscatal.0c00291,10.1021/jacs.7b04973,10.1021/acscatal.8b0343610.1039/d1ob02349g,10.1021/acs.joc.1c00204,10.1021/acs.orglett.1c02285,10.1021/jacs.1c04215,10.1039/d0cc07783f,10.1021/acs.chemrev.0c00301,10.1039/d0ob01838d,10.1002/adsc.202000794,10.1055/s-0040-1705943,10.1021/acs.chemrev.0c00088,10.1016/j.jorganchem.2020.121337,10.1021/acs.chemrev.9b00682,10.1002/anie.202004116,10.1126/science.aba3823,10.1055/s-0040-1708007,10.1039/d0sc01585g,10.1002/cjoc.201900506,10.1021/acscatal.0c00291,10.1021/acs.joc.9b02705,10.1021/acscatal.9b04586,10.1021/acs.orglett.9b02398,10.1021/acs.orglett.9b02621,10.1016/j.jcat.2019.07.026,10.1039/c9qo00536f,10.1055/s-0037-1611793,10.1021/acs.joc.8b02191,10.1039/c8sc04437f,10.1039/c8ob02140f,10.1080/02678292.2018.1468504,10.1007/3418_2018_19,10.1021/acscatal.8b03436,10.1021/acs.joc.8b02498,10.1021/acs.orglett.8b02854,10.1021/acs.joc.8b01763,10.1002/asia.201800478,10.1002/adsc.201800729,10.1039/c8ob01034j,10.1246/cl.180226,10.1016/j.jorganchem.2018.01.019,10.1021/acs.orglett.8b00974,10.1021/acs.orglett.8b00775,10.1021/acs.orglett.7b03713,10.1021/acs.orglett.8b00080,10.1055/s-0036-1591853,10.1021/acs.chemrev.7b00588,10.1021/acs.orglett.7b03669,10.1002/adsc.201700875,10.1246/cl.170798,10.1039/c7cs00182g,10.1021/jacs.7b04973,10.1021/acs.orglett.7b01905,10.1021/acscatal.7b00941,10.1021/acs.orglett.7b00556,10.1246/bcsj.20160365,10.1021/jacs.7b00049,10.1246/cl.161001,10.1021/acscatal.6b02964,10.1021/acs.orglett.6b02556Kelly#N/A
183
193FALSEacscatal.6b0200310.1021/acscatal.6b02003https://sci-hub.wf/10.1021/acscatal.6b02003https://doi.org/10.1021/acscatal.6b02003NiC-H ActivationLongTRUE794#N/A2016Punji, B
Unified Strategy for Nickel-Catalyzed C-2 Alkylation of Indoles through Chelation AssistanceACS CATAL
A nickel-catalyzed direct C-2 alkylation of indoles through monodentate-chelation assistance has been described. This reaction proceeds via an unusual strategy by the use of a well-designed and defined (quinolinyl)amido nickel catalyst, [{kappa(N),kappa(N),kappa(N)-Et2NCH2C(O)(mu-N)C9H6N}Ni(OAc)], providing a solution to the associated with bidentate-chelate auxiliaries. The method allows coupling of indoles with various unactivated primary and secondary alkyl halides with ample substrate scope. This uniquely strategized alkylation proceeded through crucial C-H activation and via an alkyl radical intermediate. The reaction by this approach represents a rare example of Ni-catalyzed monodentate-chelate-assisted C-H functionalization.
CSIR NCL9/1/2016TRUETRUEFALSEyyCsp3-Csp2_arE-NuXHXHAlkylHetLiOtBuIonic-OtBu_x10.1021/acscatal.7b01044,10.1021/acscatal.8b04267,10.1038/s41467-021-25222-1,10.1039/c9sc01446b10.1039/d2cy00027j,10.1039/d1dt03967a,10.1016/j.cclet.2021.06.091,10.1002/asia.202101208,10.1038/s41467-021-25222-1,10.1016/j.tet.2021.132309,10.1021/acs.orglett.1c01969,10.1039/d1nj01696b,10.1002/tcr.202100113,10.1039/d1nj01698a,10.1002/ajoc.202000712,10.1039/d0dt03593a,10.1021/acscatal.0c05580,10.1039/d0ob02232b,10.1021/acssuschemeng.0c07465,10.1039/d0qo00765j,10.1039/d0cc03345f,10.1021/acscatal.0c02030,10.1021/acs.orglett.0c01398,10.1016/j.chempr.2020.04.006,10.1002/adsc.202000280,10.1002/anie.202004958,10.1002/adsc.202000312,10.1002/cjoc.201900468,10.1016/j.ica.2019.119348,10.1002/ajoc.201900554,10.1039/c9sc01446b,10.1021/acs.joc.9b01375,10.1002/adsc.201900586,10.1002/adsc.201900230,10.1021/acs.joc.9b01517,10.1016/j.trechm.2019.06.002,10.1021/acs.orglett.9b01846,10.1002/anie.201806629,10.3390/catal9010076,10.1021/acscatal.8b04267,10.1039/c8dt03210f,10.1021/acscatal.8b03770,10.1021/acs.orglett.8b02812,10.1002/chem.201804077,10.1039/c8cs00201k,10.2533/chimia.2018.606,10.1002/ajoc.201800243,10.1039/c7qo01086a,10.1021/acs.organomet.8b00025,10.1021/acs.organomet.7b00902,10.1002/anie.201710089,10.1039/c8ra01377b,10.1002/chem.201702124,10.1139/cjc-2017-0258,10.1039/c7cc05532c,10.1007/s12039-017-1338-7,10.1021/acscatal.7b01337,10.1039/c7cc02808c,10.1021/acscatal.7b01044,10.1002/cssc.201700321,10.1039/c7nj00452d,10.1055/s-0036-1588936,10.1002/chem.20160530611/1/2021SEP2016FALSEFALSEFALSEFALSE695666
184
194FALSEc5sc03704b10.1039/c5sc03704bhttps://sci-hub.wf/10.1039/c5sc03704bhttps://doi.org/10.1039/c5sc03704bNiC-H ActivationGerryTRUE622472015Walsh, PJ
Nickel-catalyzed arylation of heteroaryl-containing diarylmethanes: exceptional reactivity of the Ni(NIXANTPHOS)-based catalystCHEM SCI
Nickel(0)-catalyzed cross-coupling of heteroaryl-containing diarylmethanes with both aryl bromides and chlorides has been achieved. The success of this reaction relies on the introduction of a unique nickel/NIXANTPHOS-based catalyst system, which provides a direct route to triarylmethanes from heteroaryl-containing diarylmethanes. Reactivity studies indicate the Ni(NIXANTPHOS)-based catalyst exhibits enhanced reactivity over XANTPHOS derivatives and other Ni(phosphine)-based catalysts in the reactions examined.
Univ Penn10/26/2015TRUETRUEFALSECsp3-ring(s)-Csp2_arE-NuXHBrHBenzylArylNaN(SiMe3)2IonicNitrogen(neutral)_x10.1021/jacs.7b09394,10.1038/NCHEM.274110.1039/d1qo01714d,10.1055/s-0040-1720446,10.1039/d1sc00972a,10.1002/anie.202101682,10.1039/d0sc03304a,10.1016/j.tetlet.2020.152532,10.1039/d0qo00825g,10.1002/asia.202000730,10.1002/adsc.202000622,10.1021/acs.chemrev.9b00682,10.1002/ejoc.202000077,10.1021/acs.orglett.9b03904,10.1021/jacs.9b12706,10.1039/c9ob01559k,10.1021/acs.joc.9b02094,10.1039/c9sc02448d,10.1002/adsc.201900491,10.1002/ejoc.201900465,10.1021/acs.orglett.9b01334,10.1021/acs.orglett.9b00294,10.1002/ejoc.201801596,10.1002/adsc.201801035,10.1021/jacs.8b13499,10.1002/adsc.201801045,10.1021/acs.joc.8b02549,10.1039/c8sc02965b,10.1021/acs.organomet.8b00438,10.1021/jacs.8b05143,10.1016/j.dyepig.2018.04.027,10.1002/adsc.201800396,10.1039/c8dt01852a,10.1002/anie.201713165,10.1039/c8qo00207j,10.1021/acs.joc.8b00491,10.1021/acs.joc.8b00016,10.1002/slct.201702813,10.1039/c7cy01629h,10.3390/ijerph15010116,10.1002/slct.201702244,10.1055/s-0036-1589098,10.1021/jacs.7b09394,10.1016/j.tet.2017.09.026,10.1016/j.tetlet.2017.09.022,10.1002/adsc.201700438,10.1038/NCHEM.2741,10.1021/acs.orglett.7b01510,10.1039/c7ob00911a,10.1002/ajoc.201700075,10.1016/j.bmcl.2017.02.053,10.1038/ncomms14641,10.1002/ejoc.201600955,10.1002/adsc.201600654,10.1002/slct.201600650,10.1002/adsc.201600075,10.1002/ejoc.201600385,10.1021/acs.orglett.6b00744,10.1021/acs.orglett.6b00815,10.1021/acs.orglett.6b00450,10.3762/bjoc.12.4911/22/20212016FALSEFALSEFALSEFALSE71611
185
125FALSEacscatal.7b0105810.1021/acscatal.7b01058https://sci-hub.wf/10.1021/acscatal.7b01058https://doi.org/10.1021/acscatal.7b01058NiC-O ActivationShihongTRUE66242017Uchiyama, M
Nickel-Catalyzed C-O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl ChainsACS CATALYSIS
Two efficient protocols for the nickel-catalyzed aryl alkyl cross-coupling reactions using esters as coupling components have been established. The methods enable the selective oxidative addition of nickel to acyl C-O and aryl C-O bonds and allow the aryl alkyl cross-coupling via decarbonylative bond cleavage or through cleavage of a C-O bond with high efficiency and good functional group compatibility. The protocols allow the streamlined, unconventional utilization of widespread ester groups and their precursors, carboxylic acids and phenols, in synthetic organic chemistry.
Univ Tokyo6/1/2017TRUETRUEFALSECsp2_ar-Csp2_arE-NuOAlOMe
Al(iBu)2
ArylArylNaOtBuIonic-OtBuStrong-0.28_xx10.1055/s-0036-1590863,10.1002/anie.20210332710.1039/d1ob01990b,10.1016/j.tet.2021.132564,10.1016/j.tet.2021.132549,10.1002/cssc.202101963,10.1039/d1ob01468d,10.1039/d1ob00955a,10.1039/c9cs00571d,10.1039/d1qo00759a,10.1002/anie.202103465,10.1055/a-1516-8745,10.1002/anie.202103327,10.1002/tcr.202100053,10.1039/d0cc08389e,10.1021/acs.joc.0c02992,10.1039/d0sc06056a,10.1055/a-1349-3543,10.2174/1570193X17999200723160453,10.1055/a-1337-5504,10.1021/acs.orglett.0c03507,10.1021/acscatal.0c03341,10.1021/jacs.0c08512,10.1021/acs.joc.0c01732,10.1021/acs.chemrev.0c00088,10.1248/cpb.c20-00196,10.1021/acs.organomet.0c00338,10.1021/acs.orglett.0c01127,10.1039/d0qo00173b,10.1039/c9ob02667c,10.1002/ajoc.201900759,10.1021/acs.orglett.9b04414,10.1016/bs.aihch.2020.02.001,10.1039/c9ob02107h,10.1021/jacs.9b08586,10.1021/acs.orglett.9b02923,10.1021/acs.orglett.9b02820,10.1016/j.jcat.2019.07.026,10.1002/cctc.201900047,10.1007/s12039-019-1638-1,10.1039/c9dt00455f,10.1002/chem.201900886,10.1002/aoc.4831,10.1007/3418_2018_19,10.1016/j.tet.2018.08.050,10.1002/adsc.201800729,10.1002/anie.201805486,10.6023/cjoc201803013,10.1002/anie.201804479,10.1002/chem.201801541,10.1016/j.jorganchem.2018.01.019,10.1021/acs.joc.8b00552,10.1038/s41467-018-03928-z,10.1021/acs.orglett.8b00674,10.1002/anie.201712618,10.1039/c7cc08181b,10.1039/c7cc08709h,10.1016/bs.adomc.2018.07.003,10.1055/s-0036-1590863,10.1002/asia.201701132,10.1248/cpb.c17-00487 Long 10/31/2021JUN2017FALSEFALSEFALSEFALSE763988
186
34FALSEacscatal.7b0201410.1021/acscatal.7b02014https://sci-hub.wf/10.1021/acscatal.7b02014https://doi.org/10.1021/acscatal.7b02014NiC-O ActivationKellyTRUE266382017
Stradiotto, M
Revisitation of Organoaluminurn Reagents Affords a Versatile Protocol for C X (X = N, O, F) Bond-Cleavage Cross-Coupling: A Systematic StudyACS CATALYSIS
A revisit of organoaluminum reagents for cross coupling reactions has opened up several types of C-C bond formation protocols through cleavage of phenolic/alcoholic C-O and C-F and ammonium C-N bonds. Catalyzed by the commercially available NiCl2(PCy3)(2) catalyst, these reactions proceed smoothly with a wide range of substrates and broad functional group compatibility, providing a versatile methodology for organoaluminum-mediated cross-coupling processes.
Dalhousie Univ9/1/2017Csp2_ar-Nsp3E-NuOH
OCONEt2
HAryl
N(H)Alkyl
NaOtBuIonic-OtBuMedium0.31_x10.1021/acscatal.8b01879,10.1002/anie.202014340,10.1002/anie.202002392,10.1021/jacs.8b01800,10.1021/acscatal.0c00393,10.1021/acscatal.1c0301010.1021/acscatal.1c03010,10.1021/acs.organomet.1c00369,10.1021/acs.inorgchem.1c01311,10.1039/d0qo01194k,10.1002/anie.202014340,10.1055/a-1337-6459,10.1021/acs.orglett.0c02672,10.1021/acs.orglett.0c02320,10.1021/acs.orglett.0c01600,10.1021/acscatal.0c00393,10.1002/anie.202002392,10.1021/acscatal.9b03715,10.1002/anie.201900095,10.3762/bjoc.15.48,10.1002/anie.201812862,10.1021/acs.organomet.8b00451,10.1021/acs.organomet.8b00438,10.1021/acs.joc.8b01205,10.1021/acscatal.8b01879,10.1021/acscatal.8b01005,10.1021/jacs.8b018001/5/2022
187
28FALSEacscatal.7b0261810.1021/acscatal.7b02618https://sci-hub.wf/10.1021/acscatal.7b02618https://doi.org/10.1021/acscatal.7b02618NiC-O ActivationShihongTRUE199142017Huang, ZY
Nickel-Catalyzed N-Arylation of Cyclopropylamine and Related Ammonium Salts with (Hetero)aryl (Pseudo)halides at Room TemperatureACS CATALYSIS
Whereas the metal-catalyzed C(sp(2))-N cross coupling of cyclopropylamine with aryl electrophiles represents an attractive route to pharmaceutically relevant N-arylcyclopro-pylamines, few catalysts that are capable of effecting such transformations have been identified. Herein, the nickel-catalyzed C(sp(2))-N cross-coupling of cyclopropylamine and related nucleophiles, including ammonium salts, with (hetero)aryl (pseudo)halides is reported for the first time, with the demonstrated scope of reactivity exceeding that displayed by all previously reported catalysts (Pd, Cu, or other). Our preliminary efforts to effect the N-arylation of cyclopropylamine with (hetero)aryl chlorides at room temperature by use of (L)NiCl(o-tolyl) precatalysts (L = PAd-DalPhos, Cl; L = JosiPhos CyPF-Cy, C2) were unsuccessful, despite the established efficacy of Cl and C2 in transformations of other primary alkylamines. However, systematic modification of the ancillary ligand (L) structure enabled success in such transformations, with crystallographically characterized (L)NiCl(o-tolyl) precatalysts incorporating o-phenylene-bridged bisphosphines featuring phosphatrioxaadamantane and PCy2 (L = L3, CyPAd-DalPhos; C3), P(o-tolyl)(2) and P(t-Bu)(2) (L = L4; C4), or PCy2 and P(t-Bu)(2) (L = L5; C5) donor pairings proving to be particularly effective. In employing the air-stable precatalyst C3 in cross-couplings of cyclopropylamine, substituted electrophiles encompassing an unprecedentedly broad range of heteroaryl (pyridine, isoquinoline, quinoline, quinoxaline, pyrimidine, purine, benzothiophene, and benzothiazole) and (pseudo)halide (chloride, bromide, mesylate, tosylate, triflate, sulfamate, and carbamate) structures were employed successfully, in the majority of cases under mild conditions (3 mol % of Ni, 25 degrees C). Preliminary studies also confirmed the ability of C3 to effect the N-arylation of cyclopropanemethylamine hydrochloride and cyclobutylamine hydrochloride under similar conditions. A notable exception in this chemistry was observed specifically in the case of electron-rich aryl chlorides, where the use of C4 in place of C3 proved more effective. In keeping with this observation, catalyst inhibition by 4-chloroanisole was observed in the otherwise efficient cross-coupling of cyclopropylamine and 3-chloropyridine when using C3. Competition studies involving C3 revealed a (pseudo)halide reactivity preference (Cl > Br, OTs).
Shaanxi Normal Univ SNNU
11/1/2017TRUETRUEFALSECsp2_ar-Csp2_arE-NuOHOTfHArylArylNo baseNo BaseWeak0.53_xx10.1039/c9cc03975a,10.1021/acs.joc.8b02609,10.1039/c8qo00764k,10.1002/cssc.201801443,10.1021/acscatal.9b02977,10.1021/acs.joc.7b03215,10.1021/acs.orglett.8b02256,10.1039/d0cc02261f,10.1021/jacs.9b0328010.1039/d2cc00141a,10.1039/d1cc04915a,10.1039/d1sc01430g,10.1039/d1ob00472g,10.1055/s-0040-1707266,10.1021/acs.chemrev.9b00682,10.1021/jacs.0c02860,10.1007/s41061-020-0285-9,10.1002/anie.201905174,10.1002/chem.201900921,10.1007/s00706-019-2364-6,10.1021/jacs.8b13499,10.1055/s-0037-1610273,10.1021/acs.organomet.8b00438,10.1021/acscatal.8b0023011/5/2021NOV2017FALSEFALSEFALSEFALSE7117421
188
198https://sci-hub.wf/https://doi.org/Ni345291989TAKAGI, K#N/ANICKEL(O) OR PALLADIUM(O)-CATALYZED CYANATION OF ARYL TRIFLATESCHEM LETTOKAYAMA UNIV11/1/1989_10.1016/S0040-4020(01)89366-2,10.1021/jo00126a047,10.1021/jo00041a004,10.1021/acs.joc.8b02498,10.1021/jo00106a03110.3390/molecules26041165,10.1021/acs.joc.8b02498,10.1021/acs.orglett.8b00974,10.1039/c7sc03912c,10.1021/acs.oprd.7b00285,10.1021/acs.jmedchem.5b00612,10.1055/s-0034-1379899,10.1039/c5cs00183h,10.1055/s-0034-1379483,10.1039/c4ra05203j,10.1002/asia.201200723,10.1002/chem.201102936,10.1039/c2cc17468e,10.1016/j.tetlet.2011.10.050,10.1021/cr100259t,10.1248/cpb.58.1066,10.1002/anie.201005121,10.1016/j.tetlet.2009.07.100,10.1021/ja078298h,10.1071/CH08095,10.1080/00397910701831498,10.1055/s-2007-991067,10.1016/j.tet.2007.03.028,10.1016/j.tetlet.2006.10.154,10.1080/00397910601039044,10.1039/b605732b,10.1002/ejic.200300162,10.1021/ol027256p,10.1016/S0040-4020(02)00076-5,10.1135/cccc20000729,10.1016/S0040-4039(00)00384-1,10.1021/jo991364g,10.1021/ja993071a,10.1039/a903345i,10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.3.CO;2-C,10.1016/S0040-4039(98)00414-6,10.1021/om970842f,10.1021/jo961915s,10.1021/jo00126a047,10.1139/v95-057,10.1021/jo00106a031,10.1080/00397919508015477,10.1080/00304949409458034,10.1016/S0040-4020(01)89366-2,10.1139/v93-234,10.1021/jm00073a021,10.1021/jo00041a004,10.1021/jo00028a051,10.1246/bcsj.64.1118,10.1246/cl.1990.2205,10.1016/0022-328X(90)80193-4,10.1016/0040-4039(90)80227-D,10.1016/S0040-4039(00)97053-9Kely#N/A
189
307FALSEacscatal.7b0281710.1021/acscatal.7b02817https://sci-hub.wf/10.1021/acscatal.7b02817https://doi.org/10.1021/acscatal.7b02817NiC-O ActivationJustin23-JunTRUE1321262017Banerjee, D
Mild and Efficient Ni-Catalyzed Biaryl Synthesis with Polyfluoroaryl Magnesium Species: Verification of the Arrest State, Uncovering the Hidden Competitive Second Transmetalation and Ligand-Accelerated Highly Selective MonoarylationACS CATALYSIS
Employing a nickel catalyst and electron-deficient polyfluoroaryl magnesium species, a highly selective monoarylation of polyfluoroarenes containing multiple identical coupling sites has been achieved for the first time, which represents a long-standing problem due to the competitive reactivity between the desired products and the starting polyfluoroarenes. Because of the negative fluorine effect, a surprisingly stable cis [Ni(Ar-F4)(2)(DPEPhos)] species 4 (Ar-F4 = 2,3,5,6-tetrafluorophenyl) confirmed by X-ray crystallography is isolated, which acts as catalyst arrest state as proven by a thermal decomposition test. Further retro-transmetalation experiments uncover a hidden secondary transmetalation between Ar-F4-Ni-Ph and excess Ar-F4-MgCl that competes with the desired but reluctant reductive elimination at the high-valent nickel center. Accordingly, through the cooperation of newly developed DMM-DPEPhos, and a dioxane-mediated Schlenk equilibrium with Grignard reagent, the formation of the corresponding arrest state is remarkably inhibited. An excellent coupling efficiency and an excellent monoarylation selectivity are therefore generally accomplished with a widespread electrophile scope and good functional group tolerance under mild conditions. Importantly, our novel method shows great power in the gram-scale synthesis of thienyl-2,3,5,6-tetrafluorophenyl units that represent key components in materials science.
10/20/2017Csp3-ring(s)-Nsp3E-NuOHOHHBenzyl
N(H)Aryl
t-BuOKIonic-OtBuStrong-0.817/6/2022
190
69FALSEacscatal.7b0403010.1021/acscatal.7b04030https://sci-hub.wf/10.1021/acscatal.7b04030https://doi.org/10.1021/acscatal.7b04030NiC-O ActivationGerryTRUE461312018Mazet, C
An Efficient and Selective Nickel-Catalyzed Direct N-Alkylation of Anilines with AlcoholsACS CATALYSIS
Herein, we developed an efficient and selective nickel catalyzed monoalkylation of various primary alcohols with aryl and heteroaryl amines together with diols and amino alcohol derivatives. Notably, the catalytic protocol consisting of an earth-abundant and non precious NiBr2/L1 system enables the transformations in the presence of hydroxyl, alkene, nitrile, and nitro functionalities. As a highlight, we have demonstrated the alkylation of diamine, intramolecular cyclization to N-heterocycles, and functionalization of complex vitamin E, an (+/-)-alpha-tocopherol derivative. Preliminary mechanistic studies revealed the participation of a benzylic C-H bond in the rate -determining step.
Univ Geneva2/1/2018TRUEFALSETRUECsp2-Csp2E-NuOMg
OP(O)(OEt)2
MgX
Carbonyl
VinylNo baseNo BaseStrong0.04_x10.1021/acscatal.1c0480010.1002/anie.202116870,10.1039/d1sc06364b,10.1021/acs.orglett.1c04223,10.1021/acs.orglett.1c04223,10.1021/acscatal.1c04800,10.1021/acscatal.1c04074,10.1021/acs.orglett.1c03324,10.3390/molecules26195947,10.6023/cjoc202102025,10.1021/jacs.1c06553,10.1021/acs.organomet.1c00368,10.1021/acs.joc.1c00945,10.1021/acscatal.1c01077,10.1002/app.50711,10.1039/d0qo01465f,10.1002/adsc.202001589,10.3390/molecules26020249,10.1002/ejoc.202001335,10.1021/acs.orglett.0c01892,10.1039/d0ra07472a,10.1021/acs.joc.0c01254,10.1039/d0qo00479k,10.1021/acs.orglett.0c01537,10.1021/jacs.0c00078,10.1007/s11814-020-0541-2,10.1002/anie.201913825,10.1021/acs.orglett.9b03511,10.1021/jacs.9b07253,10.1002/anie.201902903,10.1021/jacs.9b02443,10.1021/acs.organomet.8b00878,10.1055/s-0037-1611699,10.1080/00397911.2019.1566474,10.1055/s-0037-1610379,10.1021/acscatal.8b02334,10.1039/c8ob01533c,10.1021/acs.orglett.8b02073,10.1002/adsc.201800336,10.1021/acscatal.8b01380,10.1039/c8sc01538d,10.24820/ark.5550190.p010.746,10.1070/RCR4795,10.1039/c8ra07834c11/4/2021FEB2018FALSEFALSEFALSEFALSE821392
191
313FALSEacscatal.8b0295410.1021/acscatal.8b02954https://sci-hub.wf/10.1021/acscatal.8b02954https://doi.org/10.1021/acscatal.8b02954NiC-O ActivationxWilliam4-JulyTRUE251#N/A2018
Johhanes, JW
A General Nickel-Catalyzed Kumada Vinylation for the Preparation of 2-Substituted 1,3-DienesACS CATALYSIS
The identification of two nickel(II) precatalysts for the preparation of 2-substituted 1,3-dienes by a Kumada cross-coupling between vinyl magnesium bromide and vinyl phosphates is described. This is noteworthy as engaging only one vinyl derivative in a transition-metal-catalyzed cross coupling reaction is already reputedly challenging. Salient features of this method are its operational simplicity, the mild reaction conditions, the low catalyst loadings, the short reaction times, its scalability, and the use of stoichiometric quantities of each coupling partner. The tolerance of the two nickel catalysts to an important number of reactive functional groups and their compatibility with structurally complex molecular architectures has been extensively delineated. A Negishi variant of the reaction has been developed for even more sensitive organic functions such as ester or nitrile. Several other conjugated 1,3-dienes with various substitution patterns have been prepared by combining commercial alkenyl Grignard reagents and/or readily available alkenyl enol phosphates. Proper choice of the nickel catalyst and the reaction temperature gave access to a variety of different olefin isomers with high levels of stereocontrol. Overall, this approach affords conjugated dienes that would not be accessible otherwise and therefore provides a valuable complement to existing methods.
Csp3-ring(s)-Csp2_arE-EXNXN2BenzylArylNo baseNo Base7/6/2022
192
202FALSEacscatal.7b0104410.1021/acscatal.7b01044https://sci-hub.wf/10.1021/acscatal.7b01044https://doi.org/10.1021/acscatal.7b01044NiC-H ActivationKellyTRUE722#N/A2017Punji, B
Nickel-Catalyzed C(sp(2))-H/C(sp(3))-H Oxidative Coupling of Indoles with Toluene DerivativesACS CATAL
Nickel-catalyzed oxidative C(sp(2))-H/C(sp(3))-H coupling of indoles with toluene derivatives is successfully achieved in the presence of 2-iodobutane as the oxidant. This method allows the selective C-2 benzylation of indoles with toluene derivatives over the alkylation with 2-iodobutane and permits the coupling of diversified indoles via the monochelation assistance. The reaction proceeded through a single-electron-transfer (SET) process, wherein both the C-H nickelation of indole and the C-H activation of toluene derivatives have a significant effect on the entire reaction rate. The synthetic utility of this nickel-catalyzed protocol is demonstrated by the facile removal of the directing group and by the convenient synthesis of the melatonin receptor antagonist Luzindole derivatives.
Natl Chem Lab6/1/2017TRUETRUEFALSEyCsp2_ar-Csp2_arNu-NuHHHHHetHetLiOtBuIonic-OtBuNu-H_x10.1021/acscatal.8b04267,10.1039/c9sc01446b10.1039/d2cy00027j,10.1039/d1cc06507f,10.1002/asia.202101208,10.1021/acscatal.1c03314,10.1021/acs.orglett.1c02567,10.1002/asia.202100691,10.1039/d1qo00462j,10.1002/tcr.202100113,10.1039/d1nj01698a,10.1039/d1qo00340b,10.1039/d1cc01026c,10.1016/j.tetlet.2021.152950,10.1002/ajoc.202000712,10.1039/d0dt03593a,10.1002/adsc.202001498,10.2174/1385272825666210608114300,10.1021/acs.orglett.0c03535,10.1039/d0cc03345f,10.1021/acs.orglett.0c01398,10.1002/anie.202004958,10.1002/adsc.202000199,10.1002/cjoc.201900468,10.1021/acs.orglett.0c00797,10.1055/s-0039-1690218,10.1002/anie.201913930,10.1016/j.ejmech.2019.111847,10.1002/zaac.201900093,10.1002/ajoc.201900554,10.1016/j.tetlet.2019.151225,10.1039/c9sc01446b,10.1021/acs.joc.9b01375,10.1002/cjoc.201900340,10.1021/acs.joc.9b02124,10.1002/adsc.201900586,10.1002/tcr.201800093,10.1039/c9qo00644c,10.1016/j.trechm.2019.06.002,10.1002/adsc.201900105,10.1002/anie.201806629,10.1021/acs.joc.9b00237,10.1002/cctc.201900254,10.1039/c9cy00009g,10.1021/acs.organomet.8b00888,10.1021/acsomega.9b00030,10.1002/cssc.201801946,10.1021/acscatal.8b04267,10.1055/s-0037-1610342,10.1039/c8dt03210f,10.1021/acs.orglett.8b02526,10.1021/acscatal.8b02361,10.1002/ejoc.201800697,10.1002/ajoc.201800243,10.1055/s-0037-1609445,10.1039/c7qo01086a,10.1039/c7nj04880g,10.1039/c8cc00267c,10.1021/acs.orglett.7b02823,10.1039/c7cc05532c,10.1021/acs.orglett.7b02316,10.1007/s12039-017-1338-711/1/2021JUN2017FALSEFALSEFALSEFALSE764202
193
31FALSEacscatal.8b0343610.1021/acscatal.8b03436https://sci-hub.wf/10.1021/acscatal.8b03436https://doi.org/10.1021/acscatal.8b03436NiC-O ActivationShihongTRUE251242018Ong, TG
Nickel-Catalyzed Photoredox-Mediated Cross-Coupling of Aryl Electrophiles and Aryl AzidesACS CATALYSIS
Medicinally relevant diarylamines are prepared through a photoredox-mediated dual catalytic nickel/ruthenium system from aryl azides and aryl electrophiles. Photoreduction of the aryl azide is proposed to proceed through an arylnickel-azide complex, which upon reduction and loss of nitrogen, generates a nickel(III) species capable of facile reductive elimination to afford the desired C-N bond formation. A variety of functionalized (hetero)aryl electrophiles are shown to participate in the coupling, including iodides, bromides, chlorides, and triflates. The reactions are simple to set up and are performed under ambient conditions, without the exclusion of oxygen or moisture.
Acad Sinica12/1/2018TRUETRUETRUECsp2_ar-Csp2_arE-NuOHOMeHArylHetNo baseNo BaseStrong-0.28_xxx10.1016/j.chempr.2021.08.001,10.1002/anie.202107127,10.1002/chem.202100475,10.1002/poc.4250,10.1055/a-1509-5954,10.1021/jacs.1c03038,10.1055/a-1467-2494,10.1021/acs.joc.0c02389,10.1055/a-1349-3543,10.1002/chem.202002795,10.1002/ajoc.202000443,10.1021/acs.chemrev.0c00088,10.1002/asia.202000763,10.1002/aoc.5869,10.1039/d0sc01585g,10.1021/acs.joc.0c00640,10.1016/j.chempr.2020.04.005,10.1021/acs.chemrev.9b00634,10.1021/jacs.9b08342,10.1016/j.tetlet.2019.04.004,10.1055/s-0037-161166311/5/2021DEC2018FALSEFALSEFALSEFALSE81211368
194
263FALSEacscatal.9b0052110.1021/acscatal.9b00521https://sci-hub.wf/10.1021/acscatal.9b00521https://doi.org/10.1021/acscatal.9b00521NiC-O ActivationGerry5-MarTRUE41232019Wang, Y
Nickel-Catalyzed Heteroarenes Cross Coupling via Tandem C-H/C-O ActivationACS CATALYSIS
Inert aryl methyl ethers as coupling components via C-O activation have been established with a Ni catalyst for C-H activation of heteroarene. The key to simultaneous C-H/C-O bond activation is the use of sterically demanding o-tolylMgBr. The protocol is effective for a wide scope of substrates including naphthyl methyl ethers, anisoles, and a variety of other heteroarene derivatives. Detailed mechanistic studies indicated that the C-O cleavage is assisted via synergistic effect of nickel and Grignard reagent in this C-H/C-O reaction, which is supported by DFT calculation. At this stage, single-electron transfer can be ruled out as a main operative process for this tandem strategy.
4/1/2019Csp2-Csp3E-EOXOHBr
Carbonyl
AlkylNo baseNo BaseStrong-0.81_10.1002/anie.202002271,10.1021/acs.orglett.9b0116410.1002/cjoc.202100763,10.1021/acscatal.1c05073,10.1002/anie.202114731,10.1039/d1qo01219c,10.1039/d1cc04370f,10.1055/a-1637-9308,10.1021/jacs.1c07851,10.1021/acscatal.1c02913,10.1021/jacs.1c03563,10.1016/j.tetlet.2021.153108,10.1016/j.mencom.2021.03.043,10.1002/ejoc.202100005,10.1021/acscatal.1c00185,10.1002/anie.202012614,10.1021/acs.joc.0c02033,10.1021/acs.orglett.0c03342,10.1021/acs.orglett.0c03542,10.1039/d0sc03217d,10.1038/s41467-020-18658-4,10.1002/anie.202008854,10.1039/d0sc02542a,10.1002/anie.202002271,10.1002/anie.202001742,10.1002/anie.201915840,10.3390/molecules25030602,10.1002/anie.201912753,10.1021/acs.orglett.9b03871,10.1002/anie.201912629,10.1021/jacs.9b09373,10.1021/jacs.9b07489,10.1021/acs.orglett.9b02779,10.1002/chem.201903668,10.1002/ijch.201900072,10.1002/anie.201907045,10.1002/anie.201907185,10.1021/acs.orglett.9b011643/10/2022
195
205FALSEjacs.7b1360110.1021/jacs.7b13601https://sci-hub.wf/10.1021/jacs.7b13601https://doi.org/10.1021/jacs.7b13601NiC-H ActivationGerryTRUE1095382018Weix, DJ
Multimetallic Ni- and Pd-Catalyzed Cross-Electrophile Coupling To Form Highly Substituted 1,3-Dienes
J AM CHEM SOC
The synthesis of highly substituted 1,3-dienes from the coupling of vinyl bromides with vinyl triflates is reported for the first time. The coupling is catalyzed by a combination of (5,5'-bis(trifluoromethyl)2,2'-bipyridine)-NiBr-2 and (1,3-bis(diphenylphosphino)propane)PdCl2 in the presence of a zinc reductant. This method affords tetra- and penta-substituted 1,3-dienes that would otherwise be difficult to access and tolerates electron-rich and -poor substituents, heterocycles, an aryl bromide, and a pinacol boronate ester. Mechanistically, the reaction appears to proceed by an unusual zinc-mediated transfer of a vinyl group between the nickel and palladium centers.
Univ Rochester2/21/2018TRUETRUEFALSECsp2-Csp2E-NuXHBrHVinylVinylNo baseNo Base_dual catalylst10.1021/jacs.9b05461,10.1039/c9sc03347e,10.1021/acscatal.0c03993,10.1021/jacs.0c04670,10.1021/jacs.0c0133010.1038/s41467-021-27507-x,10.1002/adsc.202101388,10.1021/jacs.1c10907,10.1016/j.tet.2021.132513,10.1039/d1qo01406d,10.1021/acscatal.1c04128,10.1021/acs.orglett.1c03324,10.1039/d1ob01874d,10.1002/asia.202101004,10.1021/acscatal.1c02307,10.1021/acscatal.1c02952,10.1039/d1sc04071e,10.1055/a-1608-5693,10.1021/jacs.1c05670,10.1021/jacs.1c06236,10.1016/j.chempr.2021.06.007,10.1002/cjoc.202100034,10.1039/d1ob00791b,10.1039/d1ob00521a,10.1021/acs.orglett.1c00956,10.1002/adsc.202001589,10.1021/acs.organomet.0c00813,10.1039/d0ob02007a,10.1002/chem.202004437,10.1021/acs.orglett.0c03939,10.1021/acscatal.0c05574,10.3390/molecules26020249,10.1021/acscatal.0c04713,10.1021/acs.joc.0c02209,10.1002/anie.202012614,10.1055/s-0040-1707342,10.1007/s11426-020-9873-6,10.1021/acscatal.0c03993,10.1039/d0sc03217d,10.1039/d0qo00615g,10.1021/acs.orglett.0c02165,10.1039/d0qo00479k,10.1002/anie.202003216,10.1021/acs.chemrev.9b00682,10.1021/acs.joc.0c00549,10.1021/jacs.0c04670,10.1021/jacs.0c00078,10.1021/jacs.0c01330,10.1055/s-0039-1690769,10.1002/anie.201914215,10.1039/c9sc04127c,10.1002/anie.201909543,10.1039/c9sc03347e,10.1021/acs.orglett.9b02838,10.1002/adsc.201900626,10.1021/jacs.9b05461,10.1002/chem.201902022,10.1002/anie.201902903,10.1016/j.tet.2019.04.012,10.1002/chem.201901632,10.1021/jacs.9b02443,10.1021/acs.orglett.9b01097,10.6023/cjoc201806038,10.1055/s-0037-1610379,10.1021/jacs.8b10007,10.1021/jacs.8b08190,10.1021/jacs.8b05421,10.1039/c8ra07834c11/22/2021FEB 212018FALSEFALSEFALSEFALSE14072446
196
25FALSEacscatal.9b0074410.1021/acscatal.9b00744https://sci-hub.wf/10.1021/acscatal.9b00744https://doi.org/10.1021/acscatal.9b00744NiC-O ActivationShihongTRUE151122019Neufeldt, SR
Migratory Reductive Acylation between Alkyl Halides or Alkenes and Alkyl Carboxylic Acids by Nickel CatalysisACS CATALYSIS
A mild migratory reductive acyl cross-coupling has been achieved through NiH-catalyzed chainwalking and subsequent cross-coupling from two abundant starting materials, alkyl bromides, and carboxylic acids. This strategy allows the direct acylation of the benzylic sp(3) C-H bond with high yield as a single regioisomer. As an alternative, the alkyl bromide could be replaced by the proposed olefin intermediate and commercially available n-PrBr to achieve a remote hydroacylation process.
Montana State Univ
4/1/2019TRUETRUEFALSECsp2_ar-Csp2_arE-NuOSn
OSO2NMe2
SnBu3ArylArylNo baseNo BaseWeak0.36_xx10.1021/acscatal.1c0480010.1021/acscatal.1c04800,10.1021/acs.orglett.1c03060,10.1002/aoc.6430,10.1055/a-1548-8362,10.1021/acs.joc.1c00997,10.1016/j.jorganchem.2021.121754,10.1016/j.apcatb.2020.119425,10.1055/a-1337-5153,10.1055/a-1306-3228,10.1248/cpb.c20-00196,10.1021/acscatal.0c00618,10.1002/aoc.5662,10.1002/cjoc.201900468,10.1021/acs.orglett.9b02858 Long 11/5/2021APR2019FALSEFALSEFALSEFALSE943304
197
207FALSEja903123b10.1021/ja903123bhttps://sci-hub.wf/10.1021/ja903123bhttps://doi.org/10.1021/ja903123bNiDeletedWilliamFALSE2371#N/A2009Nguyen, HM#N/ANickel-Catalyzed Stereoselective Formation of alpha-2-Deoxy-2-Amino Glycosides
J AM CHEM SOC
The development of a new method for the stereoselective synthesis of alpha-2-deoxy-2-amino glycosides is described. This methodology relies on the nature of the cationic nickel catalyst, generated in situ from L0NiCl2 and AgOTf, to direct the anomeric stereoselectivity. The new glycosylation reaction is highly a-selective and proceeds under mild conditions with 5-10 mol % of the nickel catalyst Loading at ambient temperature. This new method has been applied to both D-glucosamine and galactosamine trichloroacetimidate donors as well as an array of primary, secondary, and tertiary alcohol nucleophiles to provide the desired glycoconjugates in good yields with excellent alpha-selectivity. Mechanistic studies of the present reaction are underway and will be reported in due course.
Montana State Univ
7/1/2009_10.1021/ja905350910.1038/s41467-022-28025-0,10.3390/molecules26216579,10.1021/acs.inorgchem.1c01038,10.1002/ejoc.202100677,10.1039/d0sc06529c,10.1021/acs.orglett.0c04178,10.1021/acs.joc.0c00703,10.1021/acscatal.0c01470,10.1021/acs.orglett.0c00101,10.1002/asia.201901621,10.1039/c9sc04079j,10.1021/jacs.9b07022,10.1021/acscatal.8b04444,10.1021/acs.chemrev.8b00144,10.1039/c7cc07332a,10.1002/anie.201708920,10.1021/acs.biomac.7b01049,10.1007/s11426-016-9010-9,10.17159/0379-4350/2017/v70a10,10.1016/j.carres.2016.10.008,10.1139/cjc-2016-0006,10.1002/ejoc.201600484,10.1002/open.201600043,10.1021/jacs.6b06943,10.1016/j.carres.2016.03.021,10.1021/jacs.5b07895,10.1002/ajoc.201500113,10.1016/j.tetlet.2015.01.016,10.1016/j.carres.2015.02.007,10.1021/acs.orglett.5b00780,10.1016/j.carres.2014.07.004,10.1002/anie.201408739,10.1080/07328303.2014.996290,10.1039/c5cc02552d,10.1039/c5sc00280j,10.1002/chem.201402433,10.5059/yukigoseikyokaishi.72.797,10.1002/tcr.201402004,10.1016/j.tet.2013.11.064,10.1002/chem.201303474,10.1039/c4qo00039k,10.1016/j.carres.2013.09.006,10.1055/s-0032-1316921,10.1039/c2cc35823a,10.1039/c3ob26994a,10.1080/07328303.2012.749264,10.1021/jo301393s,10.1002/asia.201200338,10.1021/jo301050q,10.1021/cs3002513,10.1016/j.tet.2012.04.059,10.1021/ja302640p,10.1080/07328303.2012.683910,10.1016/j.carres.2011.08.015,10.1021/ja2062715,10.1021/jo1025157,10.1039/c1ob05893b,10.1021/ja106682m,10.1021/ol1008334,10.1016/S0076-6879(10)78020-4,10.1016/j.cbpa.2009.09.013,10.1055/s-0029-1218356Kelly#N/A
198
61FALSEacscatal.9b0088410.1021/acscatal.9b00884https://sci-hub.wf/10.1021/acscatal.9b00884https://doi.org/10.1021/acscatal.9b00884NiC-O ActivationJaniceTRUE392152019Newman, SG
Nickel-Catalyzed Stille Cross Coupling of C-O ElectrophilesACS CATALYSIS
Aryl sulfamates, tosylates, and mesylates undergo efficient Ni-catalyzed cross coupling with diverse organostannanes in the presence of relatively unhindered alkylphosphine ligands and KF. The coupling is valuable for difficult bond constructions, such as aryl-heteroaryl, aryl-alkenyl, and aryl-allcynyl, using nontriflate phenol derivatives. A combination of experimental and computational studies implicates an unusual mechanism for transmetalation involving an 8-centered cyclic transition state. This reaction is inhibited by chloride sources due to slow transmetalation of organostannanes at a Ni(II)-chloride intermediate. These studies help to explain why prior efforts to achieve Ni-catalyzed Stille coupling of phenol derivatives were unsuccessful.
Univ Ottawa5/1/2019TRUETRUEFALSECsp2-Nsp3E-NuOHOMeH
Carbonyl
Morpholine
KOtBuIonic-OtBuStrong-0.28_xx10.1002/anie.202103327,10.1002/anie.20201204810.1002/ejoc.202101196,10.1039/d1cc05417a,10.1021/acs.joc.1c00931,10.1002/ejoc.202101114,10.1039/d1cy01541a,10.1002/anie.202106412,10.1038/s41467-021-24908-w,10.1039/d1ob01054a,10.1039/d1cc01795k,10.1002/anie.202103327,10.1039/d1gc01157j,10.1039/d1gc00720c,10.1021/acs.orglett.1c00940,10.1039/d0cc08389e,10.1039/d0gc03912h,10.1021/acs.joc.0c02478,10.3390/molecules26010188,10.1002/anie.202012048,10.1002/pep2.24210,10.1021/acscatal.0c03334,10.1055/s-0040-1707101,10.1021/acs.orglett.0c01676,10.1039/d0sc01349h,10.1021/acs.joc.0c00788,10.1021/acs.joc.0c00845,10.1039/d0ob00789g,10.1021/jacs.0c02405,10.1002/cmdc.201900641,10.1002/aoc.5543,10.1002/cctc.201901465,10.1039/c9cc07710c,10.1002/chem.201904717,10.1002/anie.201911372,10.1039/c9cc04634h,10.1039/c9ob01355e,10.3390/inorganics7060078 Long 11/11/2021MAY2019FALSEFALSEFALSEFALSE954426
199
301FALSEacscatal.9b0245810.1021/acscatal.9b02458https://sci-hub.wf/10.1021/acscatal.9b02458https://doi.org/10.1021/acscatal.9b02458NiC-O ActivationxWilliam12-JunTRUE171852019Molander, GA
Methyl Esters as Cross-Coupling Electrophiles: Direct Synthesis of Amide BondsACS CATALYSIS
Amide bond formation and transition metal- catalyzed cross-coupling are two of the most frequently used chemical reactions in organic synthesis. Recently, an overlap between these two reaction families was identified when Pd and Ni catalysts were demonstrated to cleave the strong C-O bond present in esters via oxidative addition. When simple methyl and ethyl esters are used, this transformation provides a powerful alternative to classical amide bond formations, which commonly feature stoichiometric activating agents. Thus far, few redox-active catalysts have been demonstrated to activate the C(acyl)-O bond of alkyl esters, which makes it difficult to perform informed screening when a challenging reaction needs optimization. We demonstrate that Ni catalysts bearing diverse NHC, phosphine, and nitrogen-containing ligands can all be used to activate methyl esters and enable their use in direct amide bond formation.
1/9/2019Csp3-Csp3E-EON
O(Ring-Opening)
diethyl 2,6-dimethyl-4-(tetrahydro-2H-pyran-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate
AlkylAlkylNo baseNo BaseWeak16/15/2022
200
35FALSEacscatal.9b0335210.1021/acscatal.9b03352https://sci-hub.wf/10.1021/acscatal.9b03352https://doi.org/10.1021/acscatal.9b03352NiC-O ActivationKellyTRUE35242019
Komeyama, K
Oxa- and Azabenzonorbornadienes as Electrophilic Partners under Photoredox/Nickel Dual CatalysisACS CATALYSIS
Herein, the introduction of oxa- and azabenzonorbornadienes into photoredox/nickel dual catalysis in a regioselective and diastereoselective transformation is disclosed. The inherent advantages of this dual catalytic system allow the use of alkyl motifs forming exclusively cis-1,2-dihydro-1-naphthyl alcohol backbones using readily accessible 4-alkyl-1,4-dihydropyridines (DHPs). Whereas previous studies have emphasized the use of nucleophilic organometallic coupling partners, this protocol grants access to a rather unexplored core featuring alkyl residues, while avoiding the use of highly reactive organometallic species (i.e., M = Al, Mg, Li, Zn, Zr). Density functional theory (DFT) calculations support an oxidative addition/reductive elimination mechanism, followed by a Curtin-Hammett scenario that controls the regioselectivity of the process, unlike previously reported transformations that proceed via a carbometalation/beta-oxygen elimination mechanism.
Hiroshima Univ10/1/2019xCsp3-Csp3E-EOXOTsBrAlkylAlkylNo baseNo BaseWeak0.36_x10.1039/d1cc02837e,10.1021/jacs.0c0133010.1021/jacs.1c10932,10.1039/d1ra08596d,10.6023/cjoc202106021,10.1016/j.ccr.2021.214165,10.1039/d1cc02837e,10.1021/acs.orglett.1c02114,10.1142/S1088424621500528,10.1021/jacs.1c00659,10.1002/anie.202102481,10.1016/j.tetlet.2021.152950,10.1002/chem.202005397,10.1039/d0ra10739e,10.1021/jacs.0c09922,10.1021/acs.chemrev.0c00245,10.1021/acscatal.0c03237,10.1021/acsomega.0c04181,10.1021/acs.orglett.0c02722,10.6023/A20070335,10.1021/acs.accounts.0c00291,10.1021/jacs.0c01330,10.1021/jacs.0c00245,10.1039/c9cc09377j,10.1002/ajoc.2019006251/16/2022
201
99FALSEcs501045v10.1021/cs501045vhttps://sci-hub.wf/10.1021/cs501045vhttps://doi.org/10.1021/cs501045vNiC-O ActivationLongTRUE546542014Garg, NK
Nickel/Cobalt-Catalyzed C(sp(3))-C(sp(3)) Cross-Coupling of Alkyl Halides with Alkyl TosylatesACS CATALYSIS
The C(sp(3))-C(sp3) Cross-Coupling of alkyl halides with alkyl tosylates has been developed by employing a combination of nickel and nucleophilic cobalt catalysts in the presence of a manganese reductant. This method provides a straightforward route to a diverse set of not only secondary-primary but also primary-primary C(sp(3))-C(sp(3)) linkages under mild conditions without using alkyl-metallic reagents. Mechanistic studies suggest the formation of alkyl radicals from both alkyl halides and alkyl tosylates. Additionally, cross-coupling could be applied to the short-step synthesis of a histone deacetylase inhibitor, Vorinostat.
Univ Calif Los Angeles
9/1/2014TRUETRUEFALSECsp2_ar-Nsp3E-NuOH
OSO2NMe2
HHet
Morpholine
NaOtBuIonic-OtBuWeak0.36_10.1038/ncomms11073,10.1039/c7cc06717h,10.1021/acscatal.6b00865,10.1002/chem.201605095,10.1002/anie.201410875,10.1021/acs.orglett.7b0055610.1039/d1sc04011a,10.1002/anie.202103803,10.1039/d0ob01874k,10.1021/acscatal.0c03334,10.1021/acs.chemrev.0c00088,10.1039/d0nj01139h,10.1039/d0cs00149j,10.1002/anie.202000124,10.1007/s11696-019-00841-7,10.1021/acs.orglett.9b02858,10.1055/s-0037-1611732,10.1039/c9gc00617f,10.1021/acs.oprd.8b00237,10.1039/c8ob01034j,10.1021/acs.orglett.7b03560,10.1021/acscatal.7b02599,10.1021/acscatal.7b03215,10.1039/c7cc06717h,10.1002/anie.201707906,10.1039/c7ob01791j,10.1055/s-0036-1588806,10.1055/s-0036-1590819,10.1002/adsc.201601271,10.1039/c7gc00067g,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1021/acs.organomet.6b00885,10.1021/acscatal.6b03277,10.1002/chem.201605611,10.1007/s00706-016-1879-3,10.1002/chem.201605095,10.1055/s-0035-1562342,10.1002/tcr.201500305,10.1021/acscatal.6b00865,10.1038/ncomms11073,10.1021/acscatal.5b02021,10.1039/c6ob01307d,10.1021/acs.oprd.5b00314,10.1002/ejoc.201500987,10.1002/ejoc.201500734,10.1021/acs.joc.5b01272,10.1002/ejoc.201500226,10.1002/adsc.201500030,10.1002/anie.201500404,10.1002/anie.201410875,10.1021/ed500158p,10.1039/c5gc01002k,10.2174/157017941206150828102108,10.1021/ja5099935Kelly12/10/2021SEP2014FALSEFALSEFALSEFALSE493289
202
213FALSEacs.orglett.9b0101410.1021/acs.orglett.9b01014https://sci-hub.wf/10.1021/acs.orglett.9b01014https://doi.org/10.1021/acs.orglett.9b01014NiC-N ActivationLongTRUE777272019Watson, MP
Deaminative Reductive Cross-Electrophile Couplings of Alkylpyridinium Salts and Aryl BromidesORG LETT
A nickel-catalyzed reductive cross-coupling of alkylpyridinium salts and aryl bromides has been developed using Mn as the reductant. Both primary and secondary alkylpyridinium salts can be used, and high functional group and heterocycle tolerance is observed, including for protic groups. Mechanistic studies indicate the formation of an alkyl radical, and controlling its fate was key to the success of this reaction.
Univ Delaware4/19/2019TRUETRUEFALSECsp3-Csp2_arE-ENX
Triphenylpyridinium+BF4-
BrAlkylArylMgCl2#N/ANo Base_Added by Yizhou10.1021/jacs.0c06904,10.1021/jacs.0c13093,10.1021/acscatal.1c05208,10.1002/anie.202002271,10.1021/acs.orglett.9b04497,10.1038/s41467-021-25222-1,10.1021/acscatal.1c0520810.1055/s-0040-1719881,10.1039/d1cs01084k,10.1021/jacs.1c12350,10.1055/s-0041-1737762,10.1021/jacs.1c12622,10.1021/acs.orglett.1c03870,10.1021/acscatal.1c05208,10.1021/jacs.1c10932,10.1021/acscatal.1c04235,10.1021/jacs.1c10150,10.1038/s41467-021-27060-7,10.1002/anie.202112454,10.1021/acscatal.1c04143,10.1021/acs.orglett.1c02708,10.1021/jacs.1c05661,10.1021/acs.orglett.1c02458,10.1038/s41467-021-25222-1,10.1021/acs.orglett.1c01959,10.1021/acs.joc.1c01018,10.1039/c9cs00571d,10.1021/acscatal.1c01860,10.1021/acs.orglett.1c01716,10.1038/s41570-021-00288-z,10.1039/d1qo00507c,10.1021/acscatal.1c01416,10.1016/j.tetlet.2021.153071,10.1039/d1sc00986a,10.1039/d1cc00039j,10.1021/acs.orglett.1c00178,10.1021/acs.orglett.1c00173,10.1021/acs.orglett.1c00346,10.1021/jacs.0c13093,10.1039/d0qo01479f,10.1039/d0cc07632e,10.1002/ejoc.202001193,10.1039/d0ob01807d,10.1021/acs.joc.0c01928,10.1039/d0cc05725h,10.1021/acscatal.0c03237,10.1039/d0cc05633b,10.1021/jacs.0c08595,10.1021/acs.joc.0c01509,10.1039/d0cc04062b,10.1021/acs.joc.0c01274,10.1021/jacs.0c06904,10.1021/acs.orglett.0c01592,10.1002/anie.202006048,10.1021/acs.oprd.0c00104,10.1021/acs.orglett.0c01284,10.1002/anie.202002271,10.1002/anie.201914555,10.1021/acs.orglett.0c00554,10.1002/anie.201911660,10.1002/chem.202000412,10.1021/acs.joc.9b02603,10.1021/acs.orglett.9b04497,10.1021/jacs.9b12167,10.1055/s-0039-1690703,10.1039/c9cc08348k,10.1039/c9cc07072a,10.1039/c9cc08333b,10.1002/chem.201905048,10.1002/asia.201901490,10.1021/acs.orglett.9b03284,10.1021/jacs.9b07489,10.1021/acscatal.9b03084,10.1021/acs.orglett.9b02643,10.1002/adsc.201900576,10.1021/acs.orglett.9b02534,10.1021/acs.orglett.9b01987,10.1038/s41929-019-0292-9Long11/14/2021
203
7FALSEja00132a03910.1021/ja00132a039https://sci-hub.wf/10.1021/ja00132a039https://doi.org/10.1021/ja00132a039NiC-O ActivationLongTRUE695881995Hoveyda, H
Nickel-Catalyzed Amination of Aryl Chlorides and Sulfamates in 2-Methyl-THF
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
The nickel-catalyzed amination of aryl O-sulfamates and chlorides using the green solvent 2-methyl-THF is reported. This methodology employs the commercially available and air-stable precatalyst NiCl2(DME), is broad in scope, and provides access to aryl amines in synthetically useful yields. The utility of this methodology is underscored by examples of gram-scale couplings conducted with catalyst loadings as low as 1 mol % nickel. Moreover, the nickel-catalyzed amination described is tolerant of heterocycles and should prove useful in the synthesis of pharmaceutical candidates and other heteroatom-containing compounds. KEYWORDS: nickel, catalysis, amination, cross-coupling 2-methyl-THF, green chemistry
07/12/1995TRUETRUEFALSECsp3-Csp2_arE-NuOMgOMeMgXAlkylArylNo baseNo BaseStrong-0.28_x10.1021/ol702122d,10.1021/ol4031364,10.1002/chem.201502329,10.1039/c1sc00026h,10.1021/jo982312e10.1021/acs.orglett.1c01879,10.1002/anie.202102233,10.1039/d1qo00370d,10.6023/cjoc202005008,10.1016/j.trechm.2020.06.002,10.1039/d0gc01194k,10.3987/REV-19-919,10.3390/molecules25030602,10.1021/acs.chemrev.8b00506,10.1002/ajoc.201800057,10.1246/cl.170533,10.1002/anie.201609654,10.1016/j.tetlet.2016.04.027,10.1002/chem.201502329,10.1039/c5ob00594a,10.1039/c5cs00144g,10.1021/ol4031364,10.1021/ja3079362,10.1002/chem.201202251,10.1002/adsc.201100809,10.1021/ja300743t,10.1007/3418_2011_10,10.1021/ja2092954,10.1021/ol2012007,10.1021/ol200059u,10.1039/c1sc00026h,10.1021/jo901728b,10.1055/s-0029-1217368,10.1021/jo802426g,10.1016/j.tetlet.2008.08.063,10.1021/om800460h,10.1021/ja7106096,10.1002/anie.200703874,10.1021/ol702122d,10.1016/j.tetlet.2007.04.017,10.1021/ol063048b,10.1055/s-2005-923611,10.1002/anie.200503274,10.1021/ja056132f,10.1055/s-2005-918455,10.1021/ja0469030,10.1016/S0022-328X(02)01173-7,10.1021/om010343l,10.1021/ja0157346,10.1021/ol0160607,10.1016/S0040-4039(00)01690-7,10.1021/ja000693j,10.1021/jo982312e,10.1021/jo982178y,10.1021/jo981745e,10.1002/(SICI)1521-3773(19991115)38:22<3386::AID-ANIE3386>3.0.CO;2-W,10.1016/S0022-328X(98)00679-2,10.1021/ja980499l,10.1021/ja980222l,10.1246/bcsj.71.973,10.1016/S0040-4020(97)10212-5,10.1021/jo9714674,10.1021/ja970885n,10.1039/co9970400136,10.1016/S0022-328X(96)06752-6,10.1039/a608612h,10.1016/S0040-4039(97)00178-0,10.1021/jo961615a,10.1021/jo960677y,10.1021/jo960458c,10.1016/0040-4039(96)00660-0Kelly3/11/2022JUL 121995FALSEFALSEFALSEFALSE117277273
204
265FALSEja00502a07410.1021/ja00502a074https://sci-hub.wf/10.1021/ja00502a074https://doi.org/10.1021/ja00502a074NiC-O ActivationGerry7-MarTRUE33262251979SWINDELL, CS
DIRECTED REGIOSELECTIVE AND STEREOSELECTIVE NICKEL-CATALYZED ADDITION OF ALKYL GRIGNARD-REAGENTS TO ALLYLIC ETHERS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
4/1/1979Csp2-Csp2_arE-NuOHOMeHVinylArylNo baseNo BaseStrong-0.28_10.1021/jacs.7b02326,10.1002/anie.200453765,10.1021/acs.orglett.5b02200,10.1021/ol4031815,10.1002/anie.200907287,10.1021/ja210249h,10.1002/anie.202012048,10.1002/anie.200900329,10.1016/j.tet.2012.04.005,10.1021/ja907700e,10.1021/ja8056503,10.1021/ja710944j,10.1021/jacs.8b02134,10.1002/chem.201003731,10.1021/ol9001587,10.1021/acscatal.6b00801,10.1021/acs.orglett.9b00242,10.1002/anie.201510497,10.1002/anie.200907359,10.1021/ol9029534,10.1002/chem.201505106,10.1002/anie.201607646,10.1021/ol9028308,10.1021/jo2000034,10.1002/anie.200803814,10.1021/acs.organomet.5b00874,10.1039/c8sc00609a,10.1002/anie.201402922,10.1038/s41929-020-00560-3,10.1021/jo00041a004,10.1039/c39880000975,10.1246/cl.150936,10.1021/acscatal.8b03436,10.1021/ol302112q,10.1021/jo00199a030,10.1021/jacs.6b03253,10.1021/acscatal.9b00744,10.1021/ol4011757,10.1021/ja810157e,10.1021/ol203322v,10.1021/acs.orglett.6b02656,10.1002/ejic.201900692,10.1021/ol901217m,10.1021/acscatal.7b01058,10.1039/c1cc11193k,10.1021/ja903091g,10.1039/c4cc08187k,10.1246/cl.1986.407,10.1002/anie.201806790,10.1002/anie.201101461,10.1021/ol502583h,10.1002/chem.200902785,10.1016/S0040-4039(01)82980-4,10.1021/ol503707m,10.1016/0040-4039(80)80215-2,10.1002/chem.201603436,10.1021/ja200398c,10.1246/cl.2009.710,10.1021/jacs.1c09797,10.1021/ol901978e,10.1002/chem.201103784,10.1021/jo00205a04210.1039/d1gc04556c,10.1021/jacs.1c09797,10.1002/anie.202110785,10.1021/acs.jpca.1c05412,10.1016/j.chempr.2021.08.001,10.1039/d1cc05408b,10.1039/d1qo00925g,10.1039/c9cs00571d,10.1039/d1sc02210e,10.1021/acs.orglett.1c01280,10.1002/asia.202100277,10.1055/a-1509-5954,10.1055/a-1507-4153,10.1021/acs.orglett.1c01053,10.1021/acscatal.1c01077,10.1021/jacs.1c03038,10.1126/science.abg5526,10.1021/acsomega.0c05936,10.1038/s41929-020-00560-3,10.1055/a-1349-3543,10.1055/s-0040-1705986,10.1002/anie.202012048,10.1021/acs.orglett.0c03507,10.1002/chem.202004132,10.1016/j.molstruc.2020.128572,10.1002/cjoc.202000319,10.1039/d0cc05271j,10.1021/acscatal.0c03334,10.1021/acs.orglett.0c02861,10.1021/acs.chemrev.0c00088,10.1039/d0cy01159b,10.1021/acs.orglett.0c02236,10.1002/cjoc.201900506,10.1039/d0cc01210f,10.1021/acs.orglett.0c00679,10.1002/anie.202001211,10.1016/j.apcatb.2019.117936,10.1021/acs.orglett.9b02504,10.1021/acs.orglett.9b02678,10.1246/cl.190393,10.1002/cjoc.201800554,10.1002/ejic.201900692,10.1007/s13738-019-01615-4,10.1002/cjoc.201800575,10.1021/acs.orglett.9b00946,10.1021/acscatal.9b00744,10.1055/s-0037-1611663,10.1021/acs.orglett.9b00242,10.1021/acs.organomet.8b00720,10.1007/3418_2018_19,10.1021/acs.accounts.8b00408,10.1002/anie.201808509,10.1021/acscatal.8b03436,10.1016/j.tet.2018.10.025,10.1002/anie.201809003,10.1039/c8gc02073f,10.1021/acs.orglett.8b02932,10.1002/cctc.201800898,10.1002/chem.201803451,10.1039/c8cc03665a,10.6023/cjoc201803013,10.1002/anie.201806237,10.1002/anie.201806790,10.1002/anie.201803760,10.1002/anie.201802434,10.1021/acs.energyfuels.8b01032,10.1039/c8cc02325e,10.1039/c8sc00609a,10.1021/acs.orglett.8b00755,10.1021/acscatal.8b01224,10.1038/s41467-018-03928-z,10.1021/acs.organomet.8b00046,10.1021/acs.orglett.8b00313,10.1021/jacs.8b02134,10.1002/ajoc.201700450,10.1002/cjoc.201700664,10.1039/c7cc08709h,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.1002/chem.201703266,10.1055/s-0036-1588568,10.1055/s-0036-1590985,10.1021/acscatal.7b03465,10.1055/s-0036-1592031,10.1002/anie.201707309,10.1021/acs.organomet.7b00632,10.1248/cpb.c17-00487,10.1021/acscatal.7b01058,10.1021/jacs.7b02326,10.1039/c7cc00078b,10.1021/acs.orglett.6b03861,10.1038/s41570-017-0025,10.1039/c6sc02895k,10.1021/acscatal.6b02964,10.1002/anie.201607646,10.1021/acs.orglett.6b02656,10.1002/ajoc.201600411,10.1021/jacs.6b10255,10.1002/chem.201604160,10.1246/cl.160712,10.1002/chem.201603436,10.1021/acs.organomet.6b00638,10.1002/asia.201600972,10.1021/jacs.6b07844,10.1002/chem.201602150,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1021/jacs.6b03253,10.1002/anie.201510497,10.1021/acs.joc.6b00289,10.1002/chem.201505106,10.1021/acscatal.5b02058,10.1016/bs.adomc.2016.07.001,10.1039/c6cc06048j,10.1021/acscatal.5b02089,10.1016/j.ccr.2015.02.004,10.1039/c5ob02212f,10.1021/acs.organomet.5b00874,10.1246/cl.150936,10.1021/jacs.5b08621,10.1021/acs.chemrev.5b00155,10.1021/acs.orglett.5b01913,10.1002/chem.201502114,10.1021/acs.orglett.5b02200,10.1002/ejoc.201500630,10.1021/acs.orglett.5b01229,10.1002/adsc.201500304,10.1016/j.tet.2015.02.088,10.1021/acs.accounts.5b00051,10.1021/acs.orglett.5b00654,10.1021/cs501498f,10.1021/ar500345f,10.1021/ja512498u,10.1021/ol503707m,10.1021/ol503560e,10.1039/c5qo00001g,10.1039/c5nj01354b,10.1039/c5sc00305a,10.1039/c4cc08187k,10.1002/anie.201402922,10.1021/ol502583h,10.1002/adsc.201400624,10.1055/s-0034-1379210,10.1021/ja503819x,10.1021/ja5043534,10.1002/adsc.201400201,10.1515/pac-2014-5038,10.1016/j.inoche.2013.12.026,10.1021/om401204h,10.1002/anie.201304268,10.1039/c4dt02374a,10.1039/c4cs00206g,10.1021/ol4031815,10.1021/ol4011757,10.1021/ja312464b,10.1016/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NICKEL-INDUCED CONVERSION OF CARBON-OXYGEN INTO CARBON-CARBON BONDS - ONE-STEP TRANSFORMATIONS OF ENOL ETHERS INTO OLEFINS AND ARYL ETHERS INTO BIARYLS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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Room-temperature Ni(0)-catalyzed cross-coupling reactions of aryl arenesulfonates with arylboronic acids
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Univ Illinois1/9/2008FALSEFALSEFALSECsp2_ar-Csp3E-NuOHOTfHArylAlkylNaOtBuIonic-OtBuWeak0.53_x10.1021/jacs.5b02945,10.1021/jo1024464,10.1039/c6ob01299j,10.1002/ejoc.200900067,10.1021/acscatal.6b00365,10.1002/anie.201412051,10.1021/ja2082087,10.1039/c4cc00959b,10.1021/jacs.1c06614,10.1002/anie.20140382310.1039/d2ob00041e,10.1038/s41467-021-27028-7,10.1039/d1ob01503f,10.1021/jacs.1c06614,10.1055/a-1560-5245,10.1021/jacs.1c05346,10.1002/anie.202106109,10.1002/eem2.12205,10.1002/tcr.202100142,10.1055/a-1503-7339,10.1021/jacs.0c13236,10.1002/asia.202001032,10.1021/acs.orglett.0c02913,10.1021/acs.joc.0c01768,10.1021/acs.orglett.0c01466,10.1021/acs.chemrev.9b00682,10.1002/aoc.5662,10.1002/ejoc.202000169,10.1021/acs.orglett.0c00333,10.1021/acscatal.9b04480,10.1021/acscatal.9b04390,10.1007/s10562-019-02929-x,10.1021/jacs.9b07514,10.1021/jacs.9b04551,10.1021/acs.joc.9b00446,10.1021/acs.orglett.9b01373,10.1021/acs.joc.9b00669,10.1002/ejoc.201900267,10.1021/acscatal.8b04357,10.1002/anie.201814475,10.1021/acs.joc.8b02478,10.1021/acscatal.8b03979,10.1002/anie.201808509,10.1002/slct.201803376,10.1021/acs.orglett.8b02084,10.1002/adsc.201800724,10.1055/s-0037-1609963,10.1016/j.tetlet.2018.06.037,10.1002/anie.201804318,10.1039/c8sc00827b,10.1021/acs.joc.8b00228,10.2174/1385272822666181015130207,10.1055/s-0036-1589120,10.1021/jacs.7b10365,10.1021/jacs.7b04937,10.1002/anie.201612385,10.1021/acs.orglett.7b00351,10.1021/acscatal.6b03355,10.1002/anie.201609930,10.1002/adsc.201600946,10.1021/jacs.6b11610,10.1021/jacs.6b09580,10.1021/acs.orglett.6b02516,10.1021/acs.organomet.6b00484,10.1021/acscatal.6b01001,10.1002/chem.201602250,10.1021/acs.organomet.6b00154,10.1021/jacs.6b01214,10.1021/acs.orglett.6b00643,10.1016/j.tet.2016.02.022,10.1007/s41061-016-0012-8,10.1021/acscatal.6b00365,10.1002/chem.201504844,10.1002/chem.201503926,10.1002/anie.201510638,10.1039/c6ob01299j,10.1039/c5nj02227d,10.1021/acs.joc.5b02098,10.1039/c5ra23417d,10.1021/jacs.5b10270,10.1021/acs.orglett.5b02370,10.1055/s-0035-1560712,10.1021/acs.orglett.5b02344,10.1021/jacs.5b02945,10.1002/anie.201412051,10.1021/cs502011x,10.1002/anie.201409065,10.1039/c5ob01203a,10.1002/chem.201405246,10.1021/ol502499q,10.1002/chem.201404398,10.1002/chem.201403446,10.1021/ol501434d,10.1002/anie.201403823,10.1016/j.tet.2013.10.017,10.1021/ol5005565,10.1021/cr4003243,10.1021/ol500292c,10.1002/ejoc.201301505,10.1021/ja411911s,10.1039/c3ob42050g,10.1021/ol403104s,10.1080/00397911.2014.880789,10.1039/c4cc00931b,10.1039/c4cc00959b,10.1039/c4qo00027g,10.1002/chem.201303384,10.1021/ol4029447,10.1021/ol402336u,10.1002/ejoc.201300934,10.1002/chem.201301869,10.1002/anie.201303602,10.1021/ja402922w,10.1021/ja403340r,10.1002/adsc.201201022,10.1002/chem.201202798,10.1039/c3cy00118k,10.1039/c3sc50806d,10.1002/anie.201300621,10.1002/anie.201300481,10.1021/ja306602g,10.1055/s-0032-1316738,10.1021/ol301713j,10.1016/j.tetlet.2012.05.146,10.1016/j.tetlet.2012.03.036,10.1021/ol300401c,10.1246/bcsj.20110307,10.1021/op3000064,10.1055/s-0031-1289650,10.1055/s-0031-1289698,10.1021/ol203303b,10.1002/adsc.201100669,10.1021/jo202012n,10.1007/128_2012_322,10.1039/c2cc36403d,10.1039/c2cc36452b,10.1055/s-0031-1290111,10.1021/om200945q,10.3762/bjoc.7.171,10.1021/ja2082087,10.1021/ja2066829,10.1021/ja206047h,10.1021/ja206050b,10.2174/138527211797248021,10.1021/jo2009164,10.1021/ol200964m,10.1002/chem.201101083,10.1021/jo200941r,10.1021/ja2039248,10.1021/ol200495a,10.1021/ol200402m,10.1021/ja2008906,10.1021/jo1024464,10.1002/ejoc.201001428,10.1021/ja110215b,10.1002/anie.201004374,10.1002/anie.201006751,10.1039/c0cy00069h,10.1002/chem.201002653,10.1039/c1ob06356a,10.1021/jo1011202,10.1021/ol101136a,10.1021/ol100666v,10.1038/NCHEM.518,10.1021/ja909689t,10.1021/cr9000836,10.1016/S0065-2725(10)09902-2,10.1002/anie.200903424,10.1002/anie.201002782,10.1002/anie.201003585,10.1071/CH09625,10.1021/ol901676f,10.1021/ja9026902,10.1021/ja903880q,10.1021/ol900719z,10.1002/ejoc.200900067,10.1021/ol900295u,10.1021/ol900362d,10.1021/ja808652a,10.1016/j.tetlet.2008.09.173,10.1021/ol802608r,10.1021/ja809220j,10.1055/s-0028-1087673,10.1002/anie.200804888,10.1002/anie.200900892,10.1055/s-2008-1078425,10.1021/ja8009428Kelly11/4/2021JAN 92008FALSEFALSEFALSEFALSE1301195
207
201FALSEja101186p10.1021/ja101186phttps://sci-hub.wf/10.1021/ja101186phttps://doi.org/10.1021/ja101186pNiC-O ActivationShihongTRUE11010662010Jamison, TF
Enantioselective alpha-arylation of ketones with aryl triflates catalyzed by difluorphos complexes of palladium and nickel
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
The asymmetric alpha-arylation of ketones with aryl triflates is described, and the use of this electrophile with nickel and palladium catalysts containing a segphos derivative increases substantially the scope of highly enantioselective arylations of ketone enolates. The combination of aryl triflates as reactant, clifluorphos as ligand, palladium catalysts for reactions of electron-neutral or electron-rich aryl triflates, and nickel catalysts for reactions of electron-poor aryl triflates led to a series of alpha-arylations of tetralone, indanone, cyclopentanone, and cyclohexanone derivatives. Enantioselectivities ranged from 70% to 98% with 10 examples over 90%. Systematic studies on these alpha-arylations have revealed a number of factors that affect enantioselectivity. Ligands containing biaryl backbones with smaller dihedral angles generate catalysts that react with higher enantioselectivity than related ligands with larger dihedral angles. In addition, faster rates for reactions of aryl triflates versus those for reactions of aryl bromides allow the a-arylations of aryl triflates to be conducted at lower temperatures, and this lower temperature improves enantioselectivity. Finally, studies that compare the enantioselectivities of catalytic reactions to those of stoichiometric reactions of isolated [(segphos)Pd(Ar)(Br)], [(segphos)Pd(Ar)(l)], and [(segphos)Ni(C6H4-4CN)Br] suggest that catalyst decomposition affects enantioselectivity.
MIT5/26/2010TRUEFALSEFALSECsp3-Csp2E-NuOAlOMe
Al(iBu)2
AllylVinylEt3NNitrogenNitrogen(neutral)Strong-0.28_x10.1021/acs.joc.6b02564,10.1002/anie.201108350,10.1021/ja2084509,10.1021/ja5026485,10.1021/acs.orglett.6b00819,10.1002/anie.201308391,10.1002/anie.201507494,10.1039/c1sc00026h,10.1021/ja209235d,10.1021/ol403181510.1021/acs.orglett.1c03720,10.1002/ejic.202100820,10.6023/cjoc202106021,10.1021/acs.orglett.1c03073,10.1021/acs.orglett.1c02938,10.1021/jacs.1c06271,10.1021/acs.orglett.1c01309,10.1039/d1qo00370d,10.1126/science.abg5526,10.1039/d0ra02912b,10.1021/acs.joc.0c00008,10.1021/jacs.0c00123,10.1021/acs.orglett.9b03633,10.1021/acs.orglett.9b02577,10.1002/adsc.201801496,10.1002/adsc.201801266,10.6023/cjoc201812051,10.1055/s-0037-1611659,10.1002/anie.201813148,10.1039/c8sc04505d,10.6023/cjoc201809037,10.1002/anie.201809112,10.1016/j.comptc.2018.09.011,10.1021/acs.joc.8b02063,10.1002/cjoc.201800237,10.1021/jacs.8b06966,10.1021/acs.orglett.8b01600,10.1016/j.isci.2018.04.020,10.1002/ajoc.201800083,10.1002/chem.201800765,10.1021/acs.orglett.8b00583,10.1055/s-0036-1590985,10.1021/acs.orglett.7b02983,10.1002/anie.201707134,10.1021/acscatal.7b01833,10.1021/acs.orglett.7b01486,10.1021/acs.orglett.7b01208,10.1021/acs.joc.6b02564,10.1016/j.tetlet.2017.03.003,10.1002/anie.201609654,10.1016/j.tetlet.2016.11.027,10.1021/acs.organomet.6b00532,10.1021/acs.orglett.6b01806,10.1248/cpb.c16-00282,10.1021/acs.orglett.6b00819,10.1002/adsc.201500822,10.1016/j.tet.2015.12.040,10.1002/anie.201507494,10.1080/00397911.2015.1127384,10.1039/c5cy02235e,10.1039/c6ra07130a,10.1021/acs.joc.5b02151,10.3762/bjoc.11.280,10.1021/acscatal.5b01075,10.1021/acs.joc.5b01240,10.1021/acs.orglett.5b01701,10.1002/anie.201503641,10.1002/anie.201503204,10.1021/acs.accounts.5b00064,10.1021/ol503607h,10.1021/jo502485u,10.1039/c5cs00144g,10.1039/c5ob00515a,10.1016/j.jorganchem.2014.08.014,10.1002/chem.201404026,10.1002/adsc.201400076,10.1021/ja5026485,10.1021/jo500068p,10.1021/ja412962w,10.1002/anie.201308391,10.1039/c4ra10203g,10.1039/c4ob00813h,10.1039/c4cc00297k,10.1039/c4cs00206g,10.1039/c4ra12251h,10.1021/ol4031815,10.1002/chem.201303668,10.1002/anie.201303916,10.3762/bjoc.9.175,10.1002/cctc.201200592,10.2174/1389557511313060003,10.1002/chem.201203694,10.1021/ja312487r,10.1039/c3cc42746c,10.1039/c3ra41690a,10.1039/c2cs35397k,10.1080/00397911.2011.604896,10.1021/ja3079362,10.1002/ejoc.201200104,10.1021/ja2084509,10.1021/om201190v,10.1039/c2cc33641c,10.1039/c1cc14593b,10.1002/anie.201108350,10.1002/anie.201200328,10.1039/c2cs35024f,10.1002/adsc.201100262,10.1021/ja209235d,10.1021/ol201702a,10.1002/asia.201000875,10.1055/s-0030-1260799,10.1021/ja201321v,10.1002/anie.201006411,10.1039/c0sc00394h,10.1039/c1sc00026h,10.1002/nadc.201178359,10.1055/s-0030-1259038Kelly11/5/2021MAY 262010FALSEFALSEFALSEFALSE132206880
208
230FALSEja108547u10.1021/ja108547uhttps://sci-hub.wf/10.1021/ja108547uhttps://doi.org/10.1021/ja108547uNiC-O ActivationShihongTRUE17031322011Jarvo, ER
Nickel-Catalyzed Allylic Substitution of Simple Alkenes
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Nickel-catalyzed intermolecular allylic substitution of simple alkenes (ethylene and alpha olefins) is described. This method is the first catalytic intermolecular process for direct allylation of nonconjugated, nonstrained simple alkenes. Catalyst loadings as low as 2.5 mol % Ni afford the desired product in high yield in both gram-scale and smaller scale coupling reactions.
Univ Calif Irvine1/26/2011TRUETRUEFALSECsp3-ring(s)-Csp3E-NuOMgOMeMgXBenzylAlkylNo baseNo BaseStrong-0.28_xx10.1021/jacs.9b00097,10.1039/c8sc00609a,10.1002/chem.201103784,10.1021/ja4034999,10.1002/anie.201101191,10.1021/ol203322v,10.1021/jacs.6b08075,10.1021/jacs.7b04973,10.1021/jacs.7b02326,10.1002/anie.201412051,10.1021/ja3089422,10.1021/ol503707m,10.1021/ja307045r,10.1002/anie.201202527,10.1021/jacs.8b13524,10.1021/acs.orglett.8b01062,10.1021/ol502583h,10.1002/anie.201308666,10.1021/ja2084509,10.1021/ol4011757,10.1002/chem.201603436,10.1021/ja5029793,10.1021/jacs.8b02134,10.1021/ol502682q,10.1021/ja5026485,10.1021/ja413131m,10.1021/ja5076426,10.1021/ja311783k,10.1021/ja300031w,10.1039/c7cc06106d,10.1021/ol300891k10.1021/acs.orglett.1c03455,10.6023/cjoc202106021,10.3390/molecules26195947,10.1021/acs.orglett.1c02458,10.1021/acs.inorgchem.1c01720,10.1021/acs.accounts.1c00050,10.1016/j.tetlet.2021.152947,10.1021/jacs.1c00618,10.1002/anie.202101682,10.3390/molecules26061615,10.1021/acs.joc.0c02556,10.1021/acs.orglett.0c04316,10.1021/acscatal.0c05484,10.1021/acs.orglett.0c04039,10.1007/s11426-020-9910-2,10.1055/s-0040-1705987,10.6023/A20070335,10.1039/d0cc02142c,10.1021/acs.chemrev.9b00682,10.1007/s11426-019-9732-5,10.1016/j.chempr.2020.01.009,10.1055/s-0039-1690718,10.1002/chem.202000215,10.1021/acs.orglett.9b03475,10.1002/ijch.201900065,10.1016/j.tetlet.2019.150955,10.1021/acs.orglett.9b01120,10.1039/c9ob00628a,10.1021/jacs.9b00097,10.1039/c8sc05261a,10.1021/jacs.8b13524,10.1002/anie.201811343,10.1021/acs.organomet.8b00720,10.1039/c8cc07093h,10.1021/acs.joc.8b01763,10.1002/anie.201806742,10.1021/jacs.8b04627,10.1021/acs.orglett.8b01807,10.1021/acscatal.8b00933,10.1016/j.jorganchem.2018.01.019,10.1039/c8sc00609a,10.1021/acs.orglett.8b01062,10.1002/cctc.201701601,10.1021/acs.orglett.8b00413,10.1021/jacs.8b02134,10.1002/cjoc.201700664,10.1002/chem.201705463,10.1021/acscatal.7b03388,10.1021/jacs.7b08326,10.1055/s-0036-1590962,10.1002/ajoc.201700324,10.1021/jacs.7b04973,10.1039/c7cc06106d,10.1002/anie.201706868,10.1021/acs.orglett.7b02287,10.1002/chem.201702200,10.1021/acs.orglett.7b01631,10.1002/anie.201703380,10.1021/jacs.7b03781,10.1021/acscatal.7b00772,10.1021/jacs.7b02326,10.1021/acs.orglett.7b01022,10.1021/acscatal.7b00300,10.1002/anie.201611720,10.1055/s-0036-1588893,10.1002/chem.201605445,10.1021/acscatal.6b03277,10.1002/chem.201603436,10.1021/acscatal.6b02124,10.1021/jacs.6b08075,10.1002/adsc.201600590,10.1021/jacs.6b04566,10.1021/jacs.6b03384,10.1002/anie.201602075,10.1021/acssuschemeng.5b01282,10.1021/acs.orglett.5b03396,10.1016/bs.adomc.2016.07.001,10.1039/c6gc00163g,10.1021/acs.joc.5b02557,10.1039/c6ra16627j,10.1002/chem.201503647,10.1021/acs.oprd.5b00148,10.1021/acs.chemrev.5b00162,10.1016/j.tet.2015.04.066,10.1002/anie.201503528,10.1021/acs.accounts.5b00223,10.1021/acs.joc.5b00991,10.1002/anie.201412051,10.1021/ar500345f,10.1021/ol503707m,10.1021/ja510980d,10.1039/c4cc10084k,10.1039/c4sc03106g,10.1016/S1872-2067(14)60217-5,10.1021/ja5109084,10.1021/ol502583h,10.1021/ol502682q,10.1021/ja5076426,10.1021/ol5024344,10.1021/ja505776m,10.1016/j.tet.2014.03.039,10.1002/chem.201402509,10.1021/ja5039616,10.1021/ja5026485,10.1021/ja5029793,10.1038/nature13274,10.1007/s40242-014-3257-1,10.1515/pac-2014-5041,10.1002/anie.201308666,10.1021/ja413131m,10.1016/j.tetlet.2013.12.083,10.1021/ja410883p,10.1039/c4cs00206g,10.1002/ejoc.201301372,10.1002/chem.201303683,10.1246/cl.130508,10.1021/ol4023358,10.1007/s11426-013-4880-2,10.1007/s40242-013-3057-z,10.1016/j.tet.2013.05.001,10.1021/ol4011757,10.1021/ja4034999,10.1021/jo400432q,10.1021/ol400289v,10.1021/ja311783k,10.1021/ja312087x,10.1021/ol303465c,10.1021/ja3089422,10.1021/ol303130j,10.1007/3418_2012_42,10.1039/c3ob27128e,10.1002/anie.201208606,10.1039/c2nj40709d,10.1002/anie.201207958,10.1039/c3cs35521g,10.1021/ja308891e,10.1021/ja3079362,10.1021/ja307045r,10.1002/ajoc.201200013,10.1021/ol300891k,10.1021/ol301442z,10.1021/ol3009842,10.1021/ol203322v,10.1002/chem.201103784,10.1021/om2005904,10.1021/ja300031w,10.1021/ja2084509,10.1002/anie.201202527,10.1039/c2cc32176a,10.1021/ja210025q,10.1055/s-0031-1289871,10.1021/jo201263r,10.1016/j.tetasy.2011.08.017,10.1021/ol201702a,10.1021/ol2012007,10.1021/om200090d,10.1021/cr100346g,10.1002/anie.201101191Kelly11/5/2021JAN 262011FALSEFALSEFALSEFALSE1333389
209
220FALSEacscatal.7b0368810.1021/acscatal.7b03688https://sci-hub.wf/10.1021/acscatal.7b03688https://doi.org/10.1021/acscatal.7b03688NiC-N ActivationGerryTRUE316542018Garg, NK
Nickel-Catalyzed Suzuki-Miyaura Coupling of Aliphatic AmidesACS CATAL
We report the Ni-catalyzed Suzuki Miyaura coupling of aliphatic amide derivatives. Prior studies have shown that aliphatic amide derivatives can undergo Ni-catalyzed carbon heteroatom bond formation but that Ni-mediated C-C bond formation using aliphatic amide derivatives has remained difficult. The coupling disclosed herein is tolerant of considerable variation with respect to both the amide-based substrate and the boronate coupling partner and proceeds in the presence of heterocycles and epimerizable stereocenters. Moreover, a gram-scale Suzuki-Miyaura coupling/Fischer indolization sequence demonstrates the ease with which unique polyheterocyclic scaffolds can be constructed, particularly by taking advantage of the enolizable ketone functionality present in the cross-coupled product. The methodology provides an efficient means to form C-C bonds from aliphatic amide derivatives using nonprecious-metal catalysis and offers a general platform for the heteroarylation of aliphatic acyl electrophiles.
Univ Calif Los Angeles
2/1/2018TRUETRUEFALSECsp2-Csp2_arE-NuNB
N(Bn)Boc
BPin
Carbonyl
HetK3PO4Ionic-PO4_x10.1021/acscatal.0c00246,10.1002/anie.202012048,10.1021/acs.orglett.9b00242,10.1021/acs.orglett.8b01021,10.1039/c8qo00764k,10.1002/anie.20200227110.1002/anie.202201142,10.1021/acscatal.1c05738,10.1039/d1ob02414k,10.1039/d1ob02349g,10.1021/acscatal.1c02790,10.1002/bkcs.12371,10.1007/s11164-021-04522-7,10.1039/c9cs00571d,10.1002/cctc.202100672,10.1021/acs.joc.0c02868,10.1039/d0cy02059a,10.1021/acs.orglett.0c03836,10.1021/acssuschemeng.0c08262,10.1016/j.tetlet.2020.152605,10.1021/acs.orglett.0c03260,10.1002/anie.202012048,10.1039/d0cc04960c,10.1002/adsc.202000794,10.1021/acscatal.0c03334,10.1039/d0qo00797h,10.1016/j.trechm.2020.08.001,10.1021/acs.organomet.0c00387,10.1002/anie.202002271,10.1021/acs.organomet.9b00834,10.1021/acscatal.0c01000,10.1039/c9tc06261k,10.1021/acs.orglett.0c00485,10.1021/acscatal.0c00246,10.1038/s41467-020-14799-8,10.1021/acs.joc.9b02826,10.1002/anie.201905838,10.1021/acs.orglett.9b03434,10.1055/s-0039-1690178,10.3390/molecules24193523,10.1039/c9cc05763c,10.1021/acs.joc.9b01699,10.1021/acs.orglett.9b02862,10.1021/acs.joc.9b01103,10.1021/acs.orglett.9b02513,10.1002/adsc.201900485,10.1038/s42004-019-0182-8,10.1021/acscatal.9b01197,10.1039/c9nj01748h,10.1039/c9qo00106a,10.1002/adsc.201801619,10.1016/j.ccr.2019.01.012,10.1021/acs.jchemed.8b00489,10.3390/molecules24071234,10.1002/chem.201802635,10.1021/acs.orglett.9b00242,10.1055/s-0037-1610664,10.1039/c8nj05503c,10.1002/asia.201801317,10.3390/catal9010053,10.1039/c8qo00764k,10.1021/acs.organomet.8b00394,10.1039/c8cs00335a,10.1039/c8cc06202a,10.1039/c8qo00591e,10.3390/molecules23102681,10.3390/molecules23102412,10.1021/acsomega.8b01598,10.1021/acs.oprd.8b00182,10.1021/acscatal.8b01380,10.1002/ejoc.201800175,10.1021/jacs.8b04637,10.1016/j.tetlet.2018.05.003,10.1021/acs.orglett.8b01021,10.1021/acs.orglett.8b00949,10.1016/j.tetlet.2018.01.097Long11/2/2021FEB2018FALSEFALSEFALSEFALSE821003
210
244FALSEja200398c10.1021/ja200398chttps://sci-hub.wf/10.1021/ja200398chttps://doi.org/10.1021/ja200398cNiC-O ActivationGerryTRUE259461222011Houk, KN
Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Ethers: Enantioselective Synthesis of Diarylethanes
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Secondary benzylic ethers undergo stereospecific substitution reactions with Grignard reagents in the presence of nickel catalysts. Reactions proceed with inversion of configuration and high stereochemical fidelity. This reaction allows for facile enantioselective synthesis of biologically active diarylethanes from readily available optically enriched carbinols.
Univ Calif Los Angeles
4/27/2011TRUEFALSEFALSECsp2_ar-Csp2_arE-NuOB
OCONEt2
B(OH)2ArylArylK3PO4Ionic-PO4Medium0.31_xx10.1021/acscatal.7b00941,10.1038/s41929-020-00560-3,10.1002/chem.201103050,10.1021/jo2022982,10.1021/acs.orglett.6b00819,10.1002/anie.201510497,10.1021/acs.orglett.7b00556,10.1021/cs501045v,10.1021/ol503061c,10.1039/c5sc02942b,10.1002/adsc.201400460,10.1039/c4qo00321g,10.1021/jo4005537,10.1021/acs.orglett.6b02265,10.1016/j.tet.2012.04.005,10.1021/jo3001194,10.1021/acscatal.9b00744,10.1021/acscatal.5b01021,10.1021/ja307045r,10.1038/nature14615,10.1038/NCHEM.2388,10.1021/ol203322v,10.1039/c1sc00230a,10.1021/acs.joc.6b01627,10.1021/jo202037x,10.1021/jacs.1c09797,10.1002/anie.201403823,10.1021/jo300547v,10.1021/ol4011757,10.1021/jacs.7b04973,10.1021/ol301847m,10.1021/acs.orglett.6b01398,10.1039/c7cc06717h,10.1021/ol302112q,10.1021/jo501291y,10.1021/ol401727y,10.1021/acscatal.7b01058,10.1021/om500452c,10.1055/s-0036-1590863,10.1021/jacs.7b04279,10.1002/ejoc.201200444,10.1021/jacs.6b11412,10.1021/ja2084509,10.1039/c4cc08426h,10.1021/acscatal.6b00801,10.1002/chem.20110378410.1021/acs.inorgchem.1c03313,10.1021/jacs.1c09797,10.1002/anie.202110785,10.1039/d1ce01282g,10.1039/d1cc05408b,10.1016/j.tet.2021.132431,10.1002/chem.202101880,10.1055/a-1548-8362,10.1021/acs.orglett.1c01280,10.1055/a-1516-8745,10.1021/acs.accounts.1c00050,10.1038/s41929-020-00560-3,10.1055/a-1349-3543,10.21577/0100-4042.20170701,10.1080/14756366.2021.1900165,10.1002/adsc.202001262,10.1002/chem.202004132,10.1021/acscatal.0c03334,10.1016/j.chempr.2020.09.004,10.1021/acs.chemrev.0c00088,10.1021/acs.jpcb.0c03844,10.1002/aoc.5662,10.1021/acs.orglett.0c01123,10.1002/cctc.202000467,10.1021/acsomega.9b04450,10.1021/acs.orglett.0c00094,10.1002/chem.202000215,10.1021/acs.organomet.9b00672,10.1021/acs.orglett.9b04119,10.1002/jccs.201900450,10.1016/j.molstruc.2019.07.054,10.1016/j.trechm.2019.08.004,10.1021/jacs.9b08586,10.1016/j.isci.2019.08.021,10.1021/acs.joc.9b01103,10.1021/acs.orglett.9b02621,10.1016/j.jcat.2019.07.026,10.1038/s42004-019-0182-8,10.1039/c9dt00455f,10.1002/adsc.201801586,10.1021/acscatal.9b00744,10.1021/acs.chemrev.8b00361,10.1039/c8nj05503c,10.1021/acs.organomet.8b00720,10.1002/anie.201809889,10.1007/3418_2018_19,10.1002/ajoc.201800610,10.1016/j.tet.2018.10.025,10.1021/acs.organomet.8b00589,10.1055/s-0037-1610273,10.1055/s-0037-1611053,10.1039/c8ob01034j,10.3390/molecules23071715,10.1021/acscatal.8b00933,10.1016/j.jorganchem.2018.01.019,10.1021/acs.orglett.8b00755,10.1016/j.tet.2018.02.053,10.7503/cjcu20170652,10.1021/acs.joc.7b03210,10.1021/acscatal.8b00230,10.1002/aoc.4273,10.1055/s-0036-1591523,10.1002/ajoc.201700645,10.1039/c7qo00934h,10.1021/acs.accounts.7b00432,10.1002/ejoc.201701142,10.1039/c7ob02386c,10.1039/c8ra01430b,10.1039/c7cc07777g,10.1039/c7ob02531a,10.1039/c7cc06717h,10.1055/s-0036-1590863,10.1055/s-0036-1590985,10.1039/c7gc02804k,10.1021/acs.orglett.7b03059,10.1039/c7dt02532g,10.1021/acs.organomet.7b00642,10.1021/jacs.7b04973,10.1016/j.jorganchem.2017.02.004,10.1021/acs.jpcc.7b06972,10.1021/acs.orglett.7b02012,10.1021/jacs.7b04279,10.1055/s-0036-1590819,10.1021/acscatal.7b00941,10.1039/c7qo00068e,10.1021/acscatal.7b01058,10.1021/acs.organomet.7b00208,10.1021/acs.orglett.7b00556,10.1021/acscatal.6b02912,10.1002/adsc.201601105,10.1021/acs.joc.6b02693,10.1021/acscatal.6b03543,10.1038/s41570-017-0025,10.1021/jacs.6b11412,10.1021/acs.jpcb.6b08644,10.1039/c6cc08759k,10.1021/acs.joc.6b02093,10.1016/j.jorganchem.2016.09.026,10.1021/acs.orglett.6b02330,10.1016/j.jorganchem.2016.08.017,10.1021/acs.joc.6b01627,10.1021/acs.orglett.6b02550,10.1007/s12274-016-1176-9,10.1021/acscatal.6b01956,10.1021/acs.orglett.6b02265,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1002/chem.201601584,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1021/acs.orglett.6b01398,10.1002/anie.201601914,10.1021/acs.orglett.6b00819,10.1002/anie.201510497,10.1021/acs.joc.6b00289,10.1021/acs.joc.6b00329,10.1021/acs.inorgchem.5b02664,10.1021/acs.orglett.5b03712,10.1016/bs.adomc.2016.07.001,10.1039/c5ra27859g,10.1039/c5nj01833a,10.1021/acscatal.5b02089,10.1038/NCHEM.2388,10.1021/acs.organomet.5b00710,10.1002/anie.201505699,10.1002/chem.201502338,10.1002/anie.201505136,10.1002/chem.201502689,10.1002/ejoc.201500987,10.1002/chem.201502114,10.1002/adsc.201500209,10.1021/acs.chemrev.5b00163,10.1002/ejoc.201500630,10.1021/acscatal.5b01021,10.1038/nature14615,10.1021/acs.orglett.5b01466,10.1016/j.tet.2015.02.088,10.3390/molecules20057528,10.1021/acs.orglett.5b00766,10.1021/ja511236d,10.1021/jo502561m,10.1016/j.jorganchem.2015.01.009,10.1021/jacs.5b00538,10.1246/cl.141084,10.1021/ed500158p,10.1021/ja512498u,10.1021/ol503560e,10.1039/c5sc02942b,10.1039/c4qo00321g,10.1039/c4qo00331d,10.1039/c4cc08426h,10.1016/j.tetlet.2014.11.020,10.1021/ol503061c,10.1021/jo502172c,10.1002/adsc.201400442,10.1021/ja5099935,10.1016/j.ica.2014.08.012,10.1021/om500452c,10.1021/ja50711741,10.1002/adsc.201400460,10.1002/chem.201404380,10.1021/jo501361k,10.1021/cs501045v,10.1007/s11426-014-5138-3,10.1016/j.ccr.2014.02.023,10.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Long 11/4/2021APR 272011FALSEFALSEFALSEFALSE133166352
211
222FALSEc9sc00783k10.1039/c9sc00783khttps://sci-hub.wf/10.1039/c9sc00783khttps://doi.org/10.1039/c9sc00783kNiC-N ActivationLongTRUE816892019Rueping, M
Nickel-catalyzed C-N bond activation: activated primary amines as alkylating reagents in reductive cross-couplingCHEM SCI
Nickel-catalyzed reductive cross coupling of activated primary amines with aryl halides under mild reaction conditions has been achieved for the first time. Due to the avoidance of stoichiometric organometallic reagents and external bases, the scope regarding both coupling partners is broad. Thus, a wide range of substrates, natural products and drugs with diverse functional groups are tolerated. Moreover, experimental mechanistic investigations and density functional theory (DFT) calculations in combination with wavefunction analysis have been performed to understand the catalytic cycle in more detail.
Rhein Westfal TH Aachen
4/28/2019TRUETRUEFALSEyyCsp2-Csp2_arE-ENX
N(Me)Ph
I
Carbonyl
ArylNo baseNo BaseReductive_xxx10.1038/s41467-021-25222-1,10.1002/anie.202002271,10.1021/jacs.0c13093,10.1021/acs.orglett.9b01016,10.1021/acs.orglett.9b04497,10.1021/acs.orglett.9b0101410.1021/acs.orglett.2c00317,10.1055/s-0040-1719881,10.1039/d1cs01084k,10.1039/d1ob02349g,10.1021/jacs.1c12350,10.1055/s-0041-1737762,10.1021/jacs.1c12622,10.1021/jacs.1c10932,10.1038/s41467-021-27060-7,10.1039/d1qo01240a,10.1002/adsc.202100940,10.1021/acs.orglett.1c02708,10.1002/ajoc.202100438,10.1016/j.jorganchem.2021.122042,10.1021/acs.orglett.1c02458,10.1038/s41467-021-25222-1,10.1039/d1nj02677a,10.1039/c9cs00571d,10.1021/acscatal.1c01860,10.1021/acs.orglett.1c01716,10.1039/d1sc01217g,10.1021/acscatal.1c01416,10.1016/j.tetlet.2021.153071,10.1039/d1sc00986a,10.1039/d1cc00039j,10.1039/d1ob00193k,10.1021/acs.orglett.1c00346,10.1021/jacs.0c13093,10.1039/d0qo01479f,10.1039/d0cc07632e,10.1002/ejoc.202001193,10.1039/d0ob01807d,10.1021/acs.joc.0c01928,10.1039/d0gc02743j,10.1021/acscatal.0c03237,10.1038/s41467-020-18834-6,10.3390/catal10091054,10.1039/d0cc04062b,10.1021/acs.joc.0c01274,10.1039/d0nj01294g,10.1021/acs.orglett.0c01592,10.1002/anie.202006048,10.1002/adsc.202000457,10.1021/acs.oprd.0c00104,10.1002/anie.202002271,10.3762/bjoc.16.74,10.1021/acs.orglett.0c00554,10.1002/anie.201915418,10.1002/anie.201911660,10.1039/d0sc00225a,10.1002/chem.202000412,10.1021/acs.orglett.9b04497,10.1039/c9qo01428d,10.1021/jacs.9b12167,10.1055/s-0039-1690703,10.1039/c9cc07072a,10.2174/1385272824999200608135840,10.1039/c9cc07558e,10.1002/chem.201905048,10.1021/acs.orglett.9b03899,10.1002/anie.201911109,10.1021/acs.orglett.9b03284,10.1021/jacs.9b07489,10.1021/acscatal.9b03084,10.1021/acs.orglett.9b02643,10.1039/c9cc05099j,10.1021/acs.orglett.9b02534,10.1002/adsc.201900803,10.1021/acs.orglett.9b01987,10.1038/s41929-019-0292-9,10.1021/acs.orglett.9b01097,10.1021/acs.orglett.9b01014,10.1021/acs.orglett.9b01016Long11/2/2021APR 282019FALSEFALSEFALSEFALSE10164430
212
223FALSEasia.20110097110.1002/asia.201100971https://sci-hub.wf/10.1002/asia.201100971https://doi.org/10.1002/asia.201100971NiC-H ActivationGerryTRUE715892012Chatani, N
Catalytic Arylation of a C?H Bond in Pyridine and Related Six-Membered N-Heteroarenes Using Organozinc ReagentsCHEM-ASIAN J
Despite significant advances in the catalytic direct arylation of heteroarenes, the application of this reaction to pyridines has been met with limited success. An oxidative nucleophilic arylation strategy has been developed to overcome this problem. Pyridine, pyrazine, quinolone, and related electron-deficient N-heteroarenes can be arylated at the most electrophilic site using the developed nickel-catalyzed reaction. This protocol serves as a complementary method to catalytic direct arylation reactions.
Osaka Univ6/1/2012yCsp2_ar-Csp2_arE-NuZnHZn(Ph)HArylHetNo baseNo Base_10.1021/ja401344e,10.1039/c5sc01589h,10.1021/ja413131m,10.1039/c5sc03704b,10.1021/acs.organomet.9b0066810.1002/jhet.4465,10.1021/acscatal.1c05266,10.1021/acs.organomet.1c00505,10.3390/molecules26185467,10.1038/s41467-021-24468-z,10.1055/a-1506-3884,10.1039/d0qo01575j,10.1021/acs.joc.0c02151,10.1021/acs.joc.0c02069,10.1002/anie.202010631,10.1021/acs.joc.0c01277,10.1021/jacs.0c06827,10.1016/j.chempr.2020.04.005,10.1021/acs.joc.9b03306,10.1021/acs.organomet.9b00668,10.1002/slct.201901144,10.1002/ajoc.201900293,10.1021/acs.chemrev.8b00507,10.1246/cl.180857,10.1021/acs.joc.8b01675,10.1016/j.ica.2018.03.036,10.1039/c7ra12716b,10.1055/s-0036-1590859,10.1021/acs.chemrev.7b00021,10.1039/c7cc00997f,10.1002/cssc.201700321,10.1007/s12272-017-0894-1,10.1039/c6qo00533k,10.1039/c6ob02079h,10.1021/acs.orglett.6b02323,10.3987/COM-16-13506,10.1007/s41061-016-0053-z,10.1021/acs.orglett.6b00932,10.1016/j.tetlet.2016.04.011,10.1002/adsc.201500445,10.1039/c6sc01457g,10.1039/c6ra01861k,10.1002/jhet.2394,10.1039/c5sc03704b,10.6023/A15040284,10.1002/adsc.201500799,10.1021/acscatal.5b01143,10.1002/chem.201500290,10.1016/j.tet.2015.03.066,10.1021/om501251q,10.1002/chem.201404635,10.1039/c5sc01589h,10.1039/c4ob01380h,10.1039/c4ra15384g,10.1002/cjoc.201400528,10.1002/chem.201403356,10.1055/s-0033-1341268,10.1002/ejoc.201301802,10.1246/bcsj.20130166,10.1021/ol403631k,10.1021/ja413131m,10.1002/asia.201301423,10.1016/j.tet.2013.09.027,10.1021/ja409803x,10.1021/ol4026827,10.1021/ol402262c,10.1002/ejoc.201300743,10.1021/ja401344e,10.1021/jo400152f,10.1021/jo302797r,10.1039/c2cy20505j,10.1002/ejoc.201200914,10.1021/ol3029059,10.1002/anie.20120611512/29/2021
213
224FALSEacs.joc.5b0066910.1021/acs.joc.5b00669https://sci-hub.wf/10.1021/acs.joc.5b00669https://doi.org/10.1021/acs.joc.5b00669NiC-H ActivationGerryTRUE722#N/A2015Li, FW
Nickel-Catalyzed Alkynylation of a C(sp(2))-H Bond Directed by an 8-Aminoquinoline MoietyJ ORG CHEM
An efficient nickel catalyst system for the direct ortho C-H alkynylation of the amides has been successfully developed with the directing assistance of 8-aminoquinoline. It was found that the flexible bis(2-dimethylaminoethyl) ether (BDMAE) ligand was critical to achieve the optimized reactivity. This protocol showed good tolerance toward not only a wide range of (hetero)aryl amides but also the rarely studied alpha,beta-unsaturated alkenyl amide. The directing amide group could be easily transformed to aldehyde or ester in high yields. Meanwhile, the removable TIPS substituent on the resultant aryl/alkenyl alkynes could be further converted to an aryl moiety through a Sila-Sonogashira coupling reaction. This Ni-catalyzed alkynylation procedure provides an alternative approach to construct a C(sp(2))-C(sp) bond.
Chinese Acad Sci6/19/2015yCsp2_ar-Csp1Nu-NuHHHHArylAlkyneNa2CO3Ionic-CO3Nu-H_xx10.1021/acscatal.6b01120,10.1039/c6qo00149a10.1002/adsc.202101365,10.1021/acs.chemrev.1c00519,10.1039/d1cc05263b,10.1002/adsc.202100992,10.1002/adsc.202100823,10.1021/acs.orglett.1c01486,10.1002/chem.202100093,10.1039/d0cs00447b,10.1016/j.tetlet.2021.152825,10.1039/d0ob02510k,10.1021/acs.orglett.0c04137,10.1039/d0ob02134b,10.1055/s-0037-1610756,10.1080/00397911.2020.1761392,10.1002/cjoc.201900468,10.1002/chem.202000411,10.1002/anie.202000935,10.1002/slct.201904651,10.1021/acs.chemrev.9b00495,10.1021/jacs.9b10868,10.1016/j.tetlet.2019.06.003,10.1039/c9cc02347j,10.1021/acs.orglett.9b00987,10.1039/c9cy00009g,10.1021/acs.organomet.8b00899,10.3390/molecules24071234,10.1039/c9nj00003h,10.1038/s42004-019-0132-5,10.1021/acs.chemrev.8b00507,10.1021/acs.organomet.8b00682,10.1039/c8ob01712c,10.1039/c8cs00201k,10.1039/c8cc03465f,10.1021/acs.organomet.8b00177,10.1002/asia.201800102,10.1021/acscatal.8b01116,10.1039/c8ob00585k,10.1021/acs.joc.8b00174,10.1039/c8ra03278e,10.1021/acs.orglett.7b02655,10.1021/acs.orglett.7b02247,10.1002/ejoc.201700788,10.1021/jacs.7b03548,10.1021/acs.orglett.7b01294,10.1039/c6qo00793g,10.1021/acs.orglett.7b00581,10.1002/chem.201700587,10.1002/chem.201606026,10.1002/chem.201605306,10.1039/c7ra11363c,10.1039/c6ob02224c,10.1002/ejoc.201600955,10.1016/j.jorganchem.2016.08.025,10.1021/acs.orglett.6b02549,10.1021/jacs.6b08171,10.1021/acs.inorgchem.6b01162,10.1007/s41061-016-0053-z,10.1021/acscatal.6b01120,10.1021/acscatal.6b00964,10.1021/acs.orglett.6b01319,10.1002/chem.201600293,10.1002/adsc.201600080,10.1021/acs.joc.6b00129,10.1002/chem.201600229,10.1002/cctc.201600039,10.1021/acs.orglett.6b00566,10.1002/adsc.201500884,10.1039/c6qo00149a,10.1039/c6cc02412b,10.1039/c6ra19583k,10.1021/acs.orglett.5b0267812/29/2021
214
225FALSEjo300209d10.1021/jo300209dhttps://sci-hub.wf/10.1021/jo300209dhttps://doi.org/10.1021/jo300209dNiC-N ActivationElaineTRUE66952012Wang, ZX
Cross-Coupling of Aryltrimethylammonium Iodides with Arylzinc Reagents Catalyzed by Amido Pincer Nickel ComplexesJ ORG CHEM
The cross-coupling reaction of aryltrimethylammonium iodides with aryl- or heteroarylzinc chlorides catalyzed by amido pincer nickel complexes was performed. The reaction requires low catalyst loading and displays broad substrate scope.
Univ Sci & Technol China
4/6/2012Csp2_ar-Csp2_arE-NuNZn
NMe3+I-
ZnXArylArylNo baseNo BaseE-H_10.1002/anie.201511197,10.1021/om500452c,10.1039/c4qo00321g,10.1016/j.tet.2017.06.004,10.1021/ja3089422,10.1126/science.abj4213,10.1039/c2dt30886j,10.1039/c3ob41989d,10.1039/c6ob01299j10.1002/adsc.202101459,10.1126/science.abj4213,10.1039/d1ob01468d,10.1039/d1qo00759a,10.1039/d1sc00757b,10.1021/acs.joc.0c02992,10.1039/d0qo00173b,10.1039/c9ob02667c,10.1021/acs.orglett.9b02820,10.1016/j.tet.2019.07.007,10.1039/c9sc01083a,10.1002/aoc.4775,10.1021/acs.joc.8b02926,10.1039/C8QO00938D,10.1002/ejic.201801179,10.1002/ajoc.201800560,10.1039/c8cc07093h,10.6023/cjoc201803013,10.1002/anie.201804628,10.1002/cctc.201702019,10.1021/acs.inorgchem.8b00958,10.6023/cjoc201710034,10.1021/acs.orglett.8b00545,10.1055/s-0036-1588548,10.1002/ajoc.201700550,10.1002/asia.201701342,10.1002/ijch.201700044,10.1002/asia.201701132,10.1016/j.tet.2017.06.004,10.1002/asia.201700313,10.1039/c7qo00174f,10.6023/cjoc201612014,10.1039/c6qo00670a,10.1039/c7ra02549a,10.1002/adsc.201600024,10.1021/acscatal.5b02718,10.1002/anie.201511197,10.1039/c6ob01299j,10.1039/c6cc04531f,10.1021/acs.joc.5b02557,10.1002/chem.201503596,10.1021/acs.chemrev.5b00386,10.1002/anie.201508161,10.1021/acs.orglett.5b02458,10.1002/ejoc.201500987,10.1021/acs.orglett.5b02380,10.1021/acs.orglett.5b01435,10.1002/adsc.201500304,10.1016/j.tetlet.2015.03.015,10.1039/c4qo00321g,10.1021/jo501665e,10.1021/om500452c,10.1016/j.inoche.2014.06.007,10.1021/ol501180q,10.1002/ejoc.201402353,10.1021/ja501649a,10.1021/jo4024123,10.1039/c3ob41989d,10.1039/c4dt00461b,10.1039/c4ob01041h,10.1016/j.tet.2013.09.039,10.1055/s-0033-1339653,10.1016/j.jorganchem.2013.06.001,10.5059/yukigoseikyokaishi.71.588,10.1021/om3011855,10.1021/ja3089422,10.1021/om3007213,10.1039/c2dt30886j12/16/2021
215
227FALSEbcsj.2014038710.1246/bcsj.20140387https://sci-hub.wf/10.1246/bcsj.20140387https://doi.org/10.1246/bcsj.20140387NiC-H ActivationGerry14-FebTRUE6010892015Chatani, N
The Nickel(II)-Catalyzed Direct Benzylation, Allylation, Alkylation, and Methylation of C-H Bonds in Aromatic Amides Containing an 8-Aminoquinoline Moiety as the Directing Group
B CHEM SOC JPN
Direct alkylation via the cleavage of the ortho C-H bonds by a nickel-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety as the directing group with alkyl halides is reported. Various alkyl halides, including benzyl, allyl, alkyl, and methyl halides (or pseudo halides) participate as electrophilic coupling partners. The reaction shows a high functional group compatibility. The reaction proceeds in a highly regioselective manner at the less hindered C-H bonds in the reaction of meta-substituted aromatic amides, irrespective of the electronic nature of the substituent. The mechanism responsible for the C-H allcylation reaction is discussed based on the results obtained in a variety of mechanistic experiments.
Osaka Univ3/15/2015yCsp3-Csp2_arE-NuOHOTsHAlkylArylNa2CO3Ionic-CO3Weak0.36_xx10.1002/anie.201511197,10.1002/anie.201510743,10.1021/acscatal.6b02003,10.1021/acs.joc.5b00669,10.1021/acs.orglett.6b00658,10.1021/acs.organomet.6b00201,10.1039/c6qo00149a,10.1039/d1cc02983e,10.1002/ajoc.201700569,10.1021/acscatal.7b0104410.1002/chem.202103077,10.1039/d1cc02983e,10.1021/acs.organomet.1c00265,10.1039/d0cs00973c,10.1055/a-1477-7059,10.1021/jacs.1c00237,10.1016/j.chempr.2020.10.020,10.1039/d0sc05813k,10.1021/acscatal.0c05580,10.1016/j.tetlet.2021.152825,10.1002/cjoc.201900468,10.1055/s-0039-1690801,10.1021/acs.chemrev.9b00634,10.1021/acs.chemrev.9b00495,10.1002/asia.201901334,10.1021/acs.joc.9b01775,10.1021/jacs.9b07857,10.1016/j.trechm.2019.06.002,10.1021/acs.orglett.9b01846,10.1002/anie.201806629,10.1039/c9cy00009g,10.1039/c8sc05063e,10.1021/acs.orglett.9b00351,10.1002/chem.201803642,10.1021/acsomega.9b00030,10.1002/ejoc.201900067,10.1021/acs.chemrev.8b00507,10.1002/ajoc.201800664,10.1021/jacs.8b07708,10.1002/ajoc.201800441,10.1039/c8cs00201k,10.1039/c8qo00438b,10.1002/ajoc.201800234,10.1039/c8ra07647b,10.1002/ajoc.201700569,10.1021/acs.orglett.7b02968,10.1002/ijch.201700044,10.1039/c7sc01750b,10.1246/bcsj.20170156,10.1055/s-0036-1589010,10.1021/jacs.7b06567,10.1021/jacs.7b03548,10.1002/slct.201701004,10.1021/acscatal.7b01044,10.1002/cssc.201700321,10.1021/acscatal.7b00159,10.1021/acs.orglett.6b02860,10.1021/acs.joc.6b01393,10.1021/acscatal.6b02003,10.1039/c6cc05330k,10.1002/chem.201602445,10.1007/s41061-016-0053-z,10.1021/acscatal.6b00964,10.1021/acs.orglett.6b01288,10.1021/acs.organomet.6b00201,10.1021/acs.joc.6b00129,10.1021/acs.orglett.6b00658,10.1002/anie.201510743,10.1002/anie.201511197,10.1002/chem.201504207,10.1002/adsc.201500791,10.1007/3418_2015_117,10.1039/c6qo00178e,10.1039/c6qo00149a,10.1021/acs.orglett.5b03142,10.1246/cl.150239,10.1021/jacs.5b04818,10.1002/chem.201500639,10.1021/acs.joc.5b00669,10.1246/cl.15004112/28/2021
216
228FALSEja505823s10.1021/ja505823shttps://sci-hub.wf/10.1021/ja505823shttps://doi.org/10.1021/ja505823sNiC-N ActivationGerryTRUE12011662014Jamison, TF
Highly Regioselective Nickel-Catalyzed Cross-Coupling of N-Tosylaziridines and Alkylzinc Reagents
J AM CHEM SOC
Herein, we report the first ligand-controlled, nickel-catalyzed cross-coupling of aliphatic N-tosylaziridines with aliphatic organozinc reagents. The reaction protocol displays complete regioselectivity for reaction at the less hindered C-N bond, and the products are furnished in good to excellent yield for a broad selection of substrates. Moreover, we have developed an air-stable nickel(II) chloride/ligand precatalyst that can be handled and stored outside a glovebox. In addition to increasing the activity of this catalyst system, this also greatly improves the practicality of this reaction, as the use of the very air-sensitive Ni(cod)(2) is avoided. Finally, mechanistic investigations, including deuterium-labeling studies, show that the reaction proceeds with overall inversion of configuration at the terminal position of the aziridine by way of aziridine ring opening by Ni (inversion), transmetalation (retention), and reductive elimination (retention).
MIT8/6/2014TRUETRUEFALSEyCsp3-Csp3E-NuNZn
N(Ring-Opening)
ZnXAlkylAlkylNo baseNo BaseNi(0)/Ni(II)_x10.1021/jacs.7b03448,10.1021/acs.orglett.8b01062,10.1021/acs.orglett.9b01014,10.1021/jacs.9b00111,10.1021/jacs.7b02389,10.1021/jacs.5b02503,10.1055/s-0037-1610084,10.1039/c9cc08079a,10.1039/c6ob01299j,10.1021/ja5076426,10.1002/chem.20140645710.1007/s11426-021-1172-x,10.3390/molecules26195947,10.1021/acs.orglett.1c02514,10.1038/s41557-021-00746-7,10.1039/d1cc01734a,10.1021/acs.orglett.1c01077,10.1002/adsc.202100195,10.1021/jacs.1c01916,10.1039/d0qo01479f,10.1055/a-1344-2434,10.1055/s-0040-1705972,10.7536/PC200607,10.1021/acs.oprd.0c00367,10.1021/acscatal.0c03341,10.1039/d0ob00535e,10.1021/jacs.0c02237,10.1021/jacs.0c01724,10.1039/c9cc08079a,10.1021/acscatal.9b04823,10.1039/c9sc02507c,10.1039/c9cc05385a,10.1039/c9cc04795f,10.1021/acscatal.9b01347,10.1021/jacs.9b05934,10.1002/chem.201902009,10.1002/chem.201901128,10.1021/acscatal.9b01191,10.1021/acs.orglett.9b01014,10.1021/jacs.9b00111,10.1021/acs.organomet.8b00720,10.1016/bs.aihch.2018.12.003,10.1021/acsomega.8b03019,10.1039/c8cc07093h,10.1055/s-0037-1610084,10.1002/anie.201802123,10.1021/acs.orglett.8b01062,10.1007/s11030-018-9829-0,10.1098/rsos.171190,10.1021/acs.orglett.7b03747,10.1039/c8ra09048c,10.6023/cjoc201702033,10.1021/jacs.7b03448,10.1021/jacs.7b02389,10.1002/adsc.201601271,10.1021/acs.orglett.7b00504,10.1021/acs.joc.7b00265,10.1039/c6cs00150e,10.1002/chem.201504596,10.1039/c6cc07855a,10.1016/bs.aihch.2016.04.002,10.1039/c6ob01299j,10.1039/c6sc01120a,10.1039/c5cs00534e,10.1021/acs.joc.5b02557,10.1002/chem.201504049,10.1021/acs.joc.5b01458,10.1021/jacs.5b06735,10.1021/jacs.5b04892,10.1002/chem.201500886,10.1021/jacs.5b02503,10.1021/acs.accounts.5b00064,10.1021/acs.orglett.5b00766,10.1002/chem.201406457,10.1039/c4cc10403j,10.1039/c4cc09321f,10.1039/c5ta00816f,10.1021/ja507642611/1/2021AUG 62014FALSEFALSEFALSEFALSE1363111145
217
213FALSEja202769t10.1021/ja202769thttps://sci-hub.wf/10.1021/ja202769thttps://doi.org/10.1021/ja202769tNiC-O ActivationKelly10-FebTRUE1357172011Biscoe, MR
Suzuki-Miyaura Cross-Coupling of Aryl Carbamates and Sulfamates: Experimental and Computational Studies
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
The first Suzuki-Miyaura cross-coupling reactions of the synthetically versatile aryl O-carbamate and O-sulfamate groups are described. The transformations utilize the inexpensive, bench-stable catalyst NiCl2(PCy3)(2) to furnish biaryls in good to excellent yields. A broad scope for this methodology has been demonstrated. Substrates with electron-donating and electron-withdrawing groups are tolerated, in addition to those that possess ortho substituents. Furthermore, heteroaryl substrates may be employed as coupling partners. A computational study providing the full catalytic cycles for these cross-coupling reactions is described. The oxidative addition with carbamates or sulfamates occurs via a five-centered transition state, resulting in the exclusive cleavage of the aryl C-O bond. Water is found to stabilize the Ni-carbamate catalyst resting state, which thus provides rationalization of the relative decreased rate of coupling of carbamates. Several synthetic applications are presented to showcase the utility of the methodology in the synthesis of polysubstituted aromatic compounds of natural product and bioactive molecule interest.
CUNY City Coll6/8/2011TRUETRUEFALSEyCsp2_ar-Csp3E-NuOMgOTfMgXArylAlkylNo baseNo BaseWeak0.53_x10.1021/ol502583h,10.1021/ja510653n,10.1021/jacs.6b08075,10.1002/anie.201705521,10.1021/jacs.7b02389,10.1002/anie.201814524,10.1021/ol403181510.1039/d1sc06422c,10.3390/polym14040716,10.1039/d1qi01486b,10.1021/acscatal.1c05530,10.1021/jacs.1c10150,10.1021/jacs.1c05902,10.1039/d1sc00900a,10.1039/d1qo00264c,10.1021/acs.organomet.0c00775,10.1039/d0cs01107j,10.1007/s13738-021-02212-0,10.1016/j.tet.2020.131804,10.1002/cctc.202001347,10.1021/acs.joc.0c01887,10.1038/s41467-020-18658-4,10.1021/acs.joc.0c01509,10.1021/acs.accounts.0c00291,10.1002/anie.202008866,10.1021/acs.orglett.0c02609,10.1039/c9ob02734c,10.1021/jacs.0c02355,10.1021/acs.jmedchem.9b01979,10.1021/jacs.0c01475,10.1039/c9cc07072a,10.1002/asia.201901179,10.1055/s-0039-1690017,10.1002/anie.201909852,10.1021/jacs.9b03991,10.1039/c9sc00554d,10.1002/adsc.201801586,10.1002/chem.201901150,10.1021/acs.organomet.8b00878,10.1016/j.cclet.2018.12.027,10.1039/c8dt04728f,10.1002/anie.201814524,10.1002/anie.201812533,10.24820/ark.5550190.p010.866,10.1039/c8cc07781a,10.1016/j.tet.2018.09.036,10.1038/s41467-018-07069-1,10.1021/jacs.8b09473,10.1021/jacs.8b09849,10.1021/acs.chemrev.8b00096,10.1055/s-0037-1609941,10.2533/chimia.2018.601,10.1021/acscatal.8b01572,10.1002/anie.201804479,10.1002/adsc.201800100,10.1021/jacs.7b10855,10.1039/c7cc08670a,10.1039/c7qo00716g,10.1070/RCR4795,10.1080/00397911.2018.1431280,10.1002/ejoc.201701654,10.1021/jacs.7b10009,10.1021/acs.orglett.7b03191,10.1021/acs.organomet.7b00613,10.1016/j.jfluchem.2017.07.017,10.1002/anie.201705521,10.1039/c7py00987a,10.1055/s-0036-1589025,10.1021/jacs.7b06567,10.1021/jacs.7b06288,10.1021/acs.orglett.7b01370,10.1021/jacs.7b02389,10.1002/anie.201609930,10.1021/jacs.6b10350,10.1021/acs.orglett.6b03090,10.1021/jacs.6b06862,10.1007/s41061-016-0067-6,10.1021/jacs.6b08075,10.1021/jacs.6b07172,10.1021/acs.orglett.6b02026,10.1021/acs.joc.6b00800,10.1021/acs.orglett.6b01745,10.1016/j.tetlet.2016.06.042,10.1002/chem.201504718,10.1021/acscatal.5b02524,10.1007/s40242-016-5261-0,10.1039/c6dt02185a,10.1039/c5cc10464e,10.1016/j.tet.2015.08.022,10.1021/jacs.5b06255,10.1002/anie.201502379,10.1021/acs.orglett.5b01418,10.1021/acs.joc.5b00794,10.1016/j.ccr.2014.12.019,10.1002/aoc.3289,10.1021/cs5014927,10.1021/ja512527s,10.1039/c4cc09594d,10.1039/c5qo00224a,10.1021/ja510653n,10.1021/ja5109084,10.1021/ol502583h,10.1016/j.jorganchem.2014.08.015,10.1021/ja508815w,10.1016/j.ica.2014.02.030,10.1021/ja5024749,10.1039/c3ob41918e,10.1021/om4010737,10.1021/ol4031815,10.1021/ja4095236,10.1002/anie.201304770,10.1055/s-0033-1339435,10.1021/ja404006w,10.1021/ja404285b,10.1038/NCHEM.1652,10.1021/jo4007046,10.1021/ja4030462,10.1021/jo400128c,10.1021/jo3027824,10.1021/ja311669p,10.1039/c3dt32111h,10.1039/c3sc51098k,10.1007/s00706-012-0838-x,10.1007/s10562-012-0913-2,10.1016/j.molcata.2012.07.007,10.1016/j.tetlet.2012.06.048,10.1021/jo301156e,10.6023/cjoc1202052,10.1055/s-0031-1290765,10.1002/chem.201103882,10.1002/anie.201204275,10.1002/anie.201205969,10.1002/anie.201104390Kelly11/10/2021JUN 82011FALSEFALSEFALSEFALSE133228478
218
200FALSEja208450910.1021/ja2084509https://sci-hub.wf/10.1021/ja2084509https://doi.org/10.1021/ja2084509NiC-O ActivationShihongTRUE1117562012Norrby, PO
Nickel-Catalyzed Kumada Cross-Coupling Reactions of Tertiary Alkylmagnesium Halides and Aryl Bromides/Triflates
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
We report a Ni-catalyzed process for the cross-coupling of tertiary alkyl nudeophiles and aryl bromides. This process is extremely general for a wide range of electrophiles and generally occurs with a ratio of retention to isomerization >30:1. The same procedure also accommodates the use of aryl triflates, vinyl chlorides, and vinyl bromides as the electrophilic component.
Univ Gothenburg1/11/2012TRUETRUEFALSECsp2_ar-Csp2E-NuOHOTfHArylVinylCy2NMeNitrogenNitrogen(neutral)Weak0.53_xx10.1021/ol203322v,10.1039/d1cc00634g,10.1002/anie.201308391,10.1021/acscatal.9b02230,10.1002/anie.201710241,10.1002/anie.202011036,10.1021/jacs.9b0328010.1039/d2qo00041e,10.1021/acscatal.1c05441,10.1002/adsc.202100585,10.1016/j.jorganchem.2021.122073,10.1021/jacs.1c05661,10.1039/d1ob00496d,10.1021/acscatal.1c00951,10.1080/00397911.2021.1919711,10.1039/d1cc00634g,10.1021/acs.orglett.1c00296,10.1039/d0dt04121a,10.1055/s-0040-1705999,10.1002/anie.202011036,10.1002/adsc.202000820,10.1039/d0cc03966g,10.1002/slct.202001578,10.1021/acs.orglett.0c02053,10.1016/j.jorganchem.2020.121354,10.1039/d0cc02142c,10.1021/acs.chemrev.9b00682,10.1016/j.tet.2020.131201,10.1002/ejoc.201901877,10.1021/jacs.0c00123,10.1016/j.tetlet.2019.151283,10.1002/anie.201911372,10.3390/inorganics7100121,10.1021/acs.orglett.9b02577,10.1021/acs.orglett.9b02130,10.1021/acscatal.9b02230,10.1055/s-0037-1611518,10.1002/anie.201812534,10.1021/acs.orglett.9b00600,10.1021/jacs.9b03280,10.1021/acs.chemrev.8b00361,10.1021/jacs.8b09401,10.1055/s-0037-1610161,10.1021/jacs.8b06966,10.1021/jacs.8b05374,10.1021/acs.orglett.8b01772,10.1021/jacs.8b03163,10.1039/c8cy00290h,10.1021/acs.orglett.8b00583,10.1002/cctc.201701617,10.1021/acs.joc.8b00377,10.1021/acs.orglett.7b03713,10.1039/c7sc04351a,10.1021/acs.orglett.7b03560,10.1080/00397911.2017.1420801,10.1002/anie.201710241,10.1002/anie.201707134,10.1002/ajoc.201700324,10.1002/anie.201706719,10.1021/jacs.7b06340,10.1021/acscatal.7b01330,10.1126/science.aan1568,10.1021/acs.chemrev.6b00692,10.1021/acs.orglett.7b01054,10.1021/acs.orglett.7b00820,10.1016/j.jclepro.2017.02.121,10.1021/acscatal.6b03277,10.1039/c7ra10755b,10.1002/chem.201604061,10.1021/acs.joc.6b01709,10.1055/s-0035-1562777,10.1055/s-0035-1562784,10.1021/acs.organomet.6b00532,10.1002/anie.201606955,10.1021/acs.chemrev.5b00695,10.1021/acs.orglett.6b01745,10.1021/acscatal.6b01816,10.1039/c6ra02989b,10.1039/c6ra01918h,10.1021/acscatal.5b02089,10.1039/c5cy02235e,10.1039/c5dt04973c,10.1021/acs.joc.5b02557,10.1055/s-0034-1380450,10.1016/j.tet.2015.08.023,10.1021/acs.chemrev.5b00163,10.1002/ejoc.201500734,10.1080/00268976.2015.1023751,10.1021/acs.chemrev.5b00052,10.1055/s-0034-1378940,10.1071/CH15459,10.1039/c5cc05312a,10.1002/adsc.201400201,10.1038/nature13274,10.1002/aoc.3134,10.1002/chem.201303249,10.1021/jo402259z,10.1002/anie.201308391,10.1021/ja4109616,10.1021/ja410118m,10.1039/c3qo00045a,10.1002/chem.201303668,10.1016/j.tetlet.2013.08.018,10.1016/j.tet.2013.07.019,10.1016/j.tetlet.2013.05.128,10.1021/ol401483j,10.1002/chem.201300127,10.1021/jo400378g,10.3762/bjoc.9.81,10.1021/op300364p,10.1039/c2dt32008h,10.1002/adsc.201200334,10.1021/ol203322v Long 11/5/2021JAN 112012FALSEFALSEFALSEFALSE1341443
219
247FALSEja210249h10.1021/ja210249hhttps://sci-hub.wf/10.1021/ja210249hhttps://doi.org/10.1021/ja210249hNiC-O ActivationShihongTRUE29534802012Itami, K
Mild and Efficient Nickel-Catalyzed Heck Reactions with Electron-Rich Olefins
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
A new efficient protocol for the nickel-catalyzed Heck reaction of aryl triflates with vinyl ethers is presented. Mild reaction conditions that equal those of the corresponding palladium-catalyzed Heck reaction are applied, representing a practical and more sustainable alternative to the conventional regioselective arylation of vinyl ethers. A catalytic system comprised of Ni(COD)(2) and 1,1'-bis(diphenylphosphino)ferrocene (DPPF) in combination with the tertiary amine Cy2NMe proved effective in the olefination of a wide range of aryl triflates. Both electron-deficient and electron-rich arenes proved compatible, and the corresponding aryl methyl ketone could be secured after hydrolysis in yields approaching quantitative. Good functional group tolerance was observed matching the characteristics of the analogous Pd-catalyzed Heck reaction. The high levels of catalytic activity were explained by the intermediacy of a cationic nickel(11) complex potentially responsible for the successive beta-hydride elimination and base promoted catalyst regeneration. Although these elementary reactions are normally considered challenging, DFT calculations suggested this pathway to be favorable under the applied reaction conditions.
Nagoya Univ1/11/2012TRUEFALSETRUECsp2_ar-Csp2_arE-NuOHOPivHArylHetCs2CO3Ionic-CO3Medium0.33_10.1002/anie.201510497,10.1002/anie.201304492,10.1016/j.tet.2012.04.005,10.1021/acscatal.7b01058,10.1021/jacs.7b04973,10.1021/ja306062c,10.1002/anie.201412051,10.1039/c5sc02942b,10.1002/chem.201103784,10.1021/acs.orglett.6b02656,10.1039/c7cc06717h,10.1021/acs.joc.5b00669,10.1021/acscatal.1c04800,10.1016/j.tet.2013.04.096,10.1021/ja401344e,10.1021/acs.orglett.6b00819,10.1002/anie.201510743,10.1021/ol203322v,10.1002/anie.202004116,10.1021/acscatal.8b03436,10.1021/ol501707z,10.1021/ol403209k,10.1039/c4cc08426h,10.1021/ja413131m,10.1002/anie.201806790,10.1002/anie.201403823,10.1021/acscatal.6b00801,10.1021/ja307045r,10.1039/c3cc46663a,10.1021/jacs.1c09797,10.1021/ol4011757,10.1039/c8sc00609a,10.1021/jacs.6b03253,10.1021/acs.orglett.6b0226510.1021/acscatal.1c04800,10.1016/j.scib.2021.08.001,10.1007/s11244-021-01527-9,10.1021/jacs.1c09797,10.1016/j.chempr.2021.08.001,10.1002/ejoc.202100660,10.3762/bjoc.17.126,10.1080/00397911.2021.1949476,10.1002/chem.202101256,10.1002/chem.202100475,10.1002/tcr.202100113,10.1002/anie.202100949,10.1039/d0sc06868c,10.1016/j.ica.2020.120191,10.1002/ejoc.202100066,10.1002/cctc.202001949,10.1016/j.cclet.2020.04.005,10.1055/a-1349-3543,10.2174/1385272825666210531110403,10.1039/d0dt01119c,10.1055/s-0040-1707208,10.1002/cjoc.202000319,10.1039/d0cy01380c,10.1021/acs.joc.0c01861,10.1021/acs.chemrev.0c00088,10.1002/asia.202000763,10.1002/anie.202006586,10.1021/acs.chemrev.9b00682,10.1002/anie.202004116,10.1021/acs.organomet.0c00338,10.1021/acs.joc.0c00530,10.3987/COM-20-14253,10.1016/j.tet.2020.131201,10.1021/acs.joc.0c00560,10.1016/j.chempr.2020.04.005,10.1002/cjoc.201900506,10.1021/acs.orglett.0c00945,10.1002/adsc.201901670,10.1002/anie.202001211,10.1021/acs.organomet.9b00629,10.1002/adsc.201901398,10.1021/acs.joc.9b02094,10.1021/acs.orglett.9b03170,10.1055/s-0037-1611895,10.1002/adsc.201900819,10.1016/j.jcat.2019.07.026,10.1039/c9cc04090k,10.1021/acs.orglett.9b01593,10.1002/adsc.201801381,10.1039/c9dt00455f,10.1039/c9ra02394a,10.1002/aoc.4914,10.1007/s10593-019-02475-9,10.1039/c8qo01365a,10.1002/chem.201805987,10.1038/s42004-019-0132-5,10.1039/c8gc03895c,10.1021/acs.chemrev.8b00507,10.1016/j.tetlet.2018.11.071,10.1007/3418_2018_19,10.3866/PKU.WHXB201810052,10.3390/catal9010076,10.1021/acs.accounts.8b00408,10.1021/acs.orglett.8b03427,10.1002/chem.201803402,10.1002/ejoc.201800533,10.1021/acscatal.8b03436,10.1016/j.tet.2018.10.025,10.1039/c8cs00036k,10.1002/asia.201800478,10.1002/adsc.201800729,10.1002/cjoc.201800166,10.1002/anie.201806790,10.1021/jacs.8b04479,10.1039/c8ob01034j,10.1055/s-0037-1610024,10.1055/s-0037-1609718,10.1039/c8qo00227d,10.1016/j.jorganchem.2018.01.019,10.1039/c8sc00609a,10.1039/c8cc01226a,10.1021/acs.orglett.8b00775,10.1002/adsc.201701506,10.1002/ajoc.201800002,10.1021/acs.organomet.8b00005,10.1002/ajoc.201700446,10.1055/s-0036-1591860,10.1021/acs.orglett.7b03713,10.1039/c7cc08709h,10.1039/c7dt04560c,10.1039/c7cc08611c,10.1021/acs.orglett.7b03669,10.1039/c7cc06717h,10.1002/aoc.3820,10.1039/c7ob02159c,10.1039/c7cs00182g,10.1021/acs.chemrev.6b00833,10.1021/jacs.7b04973,10.1039/c7cc04526c,10.1039/c7qo00318h,10.1021/acsomega.7b01165,10.1021/acs.orglett.7b01938,10.1002/chem.201605657,10.1021/jacs.7b05574,10.1002/adsc.201700290,10.1039/c7qo00174f,10.1039/c7qo00068e,10.1021/acscatal.7b01058,10.1002/ejoc.201700290,10.1016/j.tetlet.2017.04.001,10.1021/acs.orglett.7b01022,10.1016/j.tet.2017.02.021,10.1246/bcsj.20160365,10.1021/acscatal.7b00094,10.1002/anie.201611720,10.1021/jacs.7b00049,10.1002/hc.21360,10.1021/acscatal.6b02988,10.1021/acscatal.7b00245,10.1002/anie.201610409,10.1021/acscatal.6b03277,10.1021/jacs.6b12329,10.1039/c6cs00150e,10.1021/acscatal.6b02964,10.1021/acs.joc.6b01836,10.1021/acs.orglett.6b02656,10.1021/acs.organomet.6b00655,10.1002/ejoc.201600955,10.1021/acscatal.6b02477,10.1021/acs.orglett.6b02556,10.1021/jacs.6b04789,10.1021/acscatal.6b01956,10.1002/anie.201606529,10.1016/j.tet.2016.07.082,10.1002/cctc.201600589,10.1021/acs.orglett.6b02265,10.1002/chem.201603092,10.1007/s41061-016-0043-1,10.1007/s41061-016-0053-z,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1002/anie.201602075,10.1021/acs.orglett.6b00819,10.1021/jacs.6b03253,10.1002/anie.201510497,10.1021/acs.joc.6b00289,10.1246/cl.160133,10.1002/anie.201512027,10.1002/chem.201504959,10.1021/acs.orglett.6b00195,10.1002/adsc.201500822,10.1021/acscatal.5b02058,10.1002/anie.201510743,10.1016/j.jorganchem.2015.12.009,10.1016/bs.adomc.2016.07.001,10.1039/c6ra18510j,10.2174/1385272819666150423202719,10.1039/c6ob00607h,10.1039/c5cc10005d,10.1021/acscatal.5b02089,10.1016/bs.aihch.2016.04.005,10.1039/c6ra07130a,10.6023/A15040284,10.1515/hc-2015-0137,10.1021/acs.joc.5b01450,10.1002/asia.201500599,10.1021/acs.orglett.5b02458,10.1002/ejoc.201500987,10.1002/adsc.201500515,10.1021/acs.chemrev.5b00163,10.1002/anie.201503204,10.1055/s-0034-1379927,10.1016/j.tet.2015.02.088,10.1016/j.tet.2015.03.066,10.1021/acs.joc.5b00669,10.1002/anie.201502942,10.1038/ncomms8508,10.1021/acs.accounts.5b00051,10.1002/ejic.201500148,10.1002/anie.201412051,10.1021/acs.orglett.5b00510,10.1021/ja511730k,10.1246/cl.141084,10.1021/ol503607h,10.1021/ja512498u,10.1055/s-0034-1379890,10.1021/ja5116452,10.1002/anie.201403729,10.1039/c5sc02942b,10.1039/c5dt00032g,10.1039/c5sc00305a,10.1039/c5cc02254a,10.3998/ark.5550190.p008.915,10.1039/c4ob02488e,10.1039/c4cc10431e,10.1007/s10562-014-1449-4,10.1039/c4cc08426h,10.1039/c4cc10084k,10.1016/S1872-2067(14)60217-5,10.1021/ol502815p,10.1002/ejoc.201402751,10.1039/c4dt02313g,10.1055/s-0034-1378555,10.1021/ja50711741,10.1021/jo501361k,10.1016/j.tet.2014.07.022,10.5012/bkcs.2014.35.8.2304,10.1021/ol5019135,10.1021/ol501707z,10.1002/chem.201403356,10.1021/cs500587b,10.3987/COM-14-12996,10.1002/anie.201403823,10.1002/ejoc.201402129,10.1038/nature13274,10.1021/ol500531m,10.1515/pac-2014-5033,10.1515/pac-2014-5038,10.1246/bcsj.20130166,10.1021/jo4025573,10.1021/ja413131m,10.1021/ja4118413,10.1021/ja410883p,10.1021/ol403209k,10.1039/c4cc05307a,10.1039/c3sc52199k,10.1039/c4cs00206g,10.1039/c4gc01572j,10.1039/c4ob01061b,10.1021/jo402106q,10.1016/j.tet.2013.10.043,10.1021/ol4027073,10.1021/ja409803x,10.1002/ajoc.201300172,10.1007/s11243-013-9759-8,10.1021/ol402494e,10.1021/om400711d,10.1002/anie.201304492,10.1021/jo400949p,10.1016/j.tet.2013.05.138,10.1016/j.tet.2013.04.096,10.1021/ol4011757,10.1002/aoc.3000,10.1021/jo400692p,10.5059/yukigoseikyokaishi.71.576,10.1021/ol400537b,10.1021/ja401344e,10.1021/ol303567t,10.1007/3418_2012_42,10.1039/c3cc46663a,10.1039/c2cy20505j,10.1002/anie.201208843,10.1039/c3cc43915a,10.1039/c2dt32008h,10.1002/ejoc.201200914,10.3987/COM-12-S(N)94,10.1021/jo3021192,10.1038/pj.2012.89,10.1021/ja306992k,10.1021/ol302166n,10.1016/j.tet.2012.05.091,10.1021/ja307045r,10.1021/ja306062c,10.1016/j.tetlet.2012.05.155,10.1021/ol301615z,10.1002/chem.201201394,10.1016/j.tet.2012.04.005,10.1021/ol300570f,10.1021/ol300671y,10.1021/ol203322v,10.1002/chem.201103784,10.1039/c2cc34238c,10.1002/anie.201202466,10.1002/anie.201201666,10.1039/c2sc20277h Long 11/5/2021JAN 112012FALSEFALSEFALSEFALSE1341169
220
167FALSEja300031w10.1021/ja300031whttps://sci-hub.wf/10.1021/ja300031whttps://doi.org/10.1021/ja300031wNiC-O ActivationShihongTRUE885972012Fu, GC
Nickel-Catalyzed C-H/C-O Coupling of Azoles with Phenol Derivatives
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
The first nickel-catalyzed C-H bond arylation of azoles with phenol derivatives is described. The new Ni(cod)(2)/dcype catalytic system is active for the coupling of various phenol derivatives such as esters, carbamates, carbonates, sulfamates, triflates, tosylates, and mesylates. With this C-H/C-O biaryl coupling, we synthesized a series of privileged 2-arylazoles, including biologically active alkaloids. Moreover, we demonstrated the utility of the present reaction for functionalizing estrone and quinine.
MIT2/15/2012TRUETRUEFALSECsp3-Csp2_arE-NuOZn
OCO2(2,4,6-trimethoxyphenyl)
ZnXAlkylArylNo baseNo BaseStrong0.13_x10.1021/ja4034999,10.1021/ja408561b,10.1021/ol3013342,10.1021/jacs.0c06904,10.1021/ol403136410.1002/anie.202117114,10.1021/acs.orglett.1c04086,10.1021/acs.orglett.1c04086,10.1021/acscatal.1c04235,10.1039/d1sc06038d,10.1039/d1ob01944a,10.1021/acscatal.1c04143,10.1016/j.ccr.2021.214165,10.1021/acs.joc.1c00474,10.1002/ejoc.202100367,10.1039/d1cc00203a,10.1021/jacs.0c13034,10.1002/chem.202004413,10.1021/acs.orglett.0c04039,10.1002/ajoc.202000422,10.1039/d0cc04986g,10.1055/a-1282-9731,10.1021/jacs.0c06904,10.1002/anie.202005019,10.1021/jacs.0c02876,10.1002/adsc.201901203,10.6023/A19060201,10.1002/ajoc.201900409,10.1021/jacs.9b05671,10.1002/chir.23085,10.1021/jacs.9b02338,10.1016/j.molstruc.2018.09.034,10.1002/anie.201813222,10.1039/c8cc07093h,10.1002/ejoc.201800849,10.1021/acs.joc.8b01498,10.1021/acs.orglett.8b02325,10.1055/s-0036-1591997,10.1002/anie.201803668,10.1002/ajoc.201800094,10.1038/s41557-018-0021-z,10.1002/cjoc.201700745,10.1002/chem.201705463,10.1002/anie.201711155,10.1039/c7cy01382e,10.1039/c8ra04481c,10.1055/s-0036-1589057,10.1055/s-0036-1590962,10.1021/jacs.7b09802,10.1021/acscentsci.7b00212,10.1021/jacs.7b03781,10.1021/acscatal.7b00772,10.1021/jacs.7b02455,10.1021/acs.chemrev.6b00731,10.1021/jacs.6b13299,10.1002/chem.201603758,10.1021/acs.orglett.6b02933,10.1007/s41061-016-0067-6,10.1021/acs.orglett.6b01642,10.1021/jacs.6b03384,10.1246/cl.150913,10.1039/c6sc01086e,10.1021/acs.chemrev.5b00162,10.1002/ejoc.201500734,10.1002/adsc.201400850,10.1021/jacs.5b02277,10.1016/S1872-2067(14)60217-5,10.1002/ejoc.201402713,10.3390/molecules190913603,10.1021/ol4031364,10.1039/c3qo00066d,10.6023/cjoc201307014,10.1002/adsc.201300720,10.1021/ja408561b,10.1055/s-0033-1339435,10.1021/ja4051923,10.1002/chem.201300241,10.1016/j.tet.2013.05.001,10.1021/ja4034999,10.1021/ja4030462,10.1021/ja401466y,10.3998/ark.5550190.0014.205,10.1021/ja308460z,10.1002/chem.201201607,10.1021/ol3013342,10.1021/ja304068t,10.1021/ja303442q,10.1021/ja209572mKelly11/5/2021FEB 152012FALSEFALSEFALSEFALSE13462966
221
234FALSEjacs.8b1352410.1021/jacs.8b13524https://sci-hub.wf/10.1021/jacs.8b13524https://doi.org/10.1021/jacs.8b13524NiC-H ActivationLongTRUE462#N/A2019Mei, TS
Nickel-catalyzed Enantioselective Hydroarylation and Hydroalkenylation of Styrenes
J AM CHEM SOC
We have developed a Ni-catalyzed enantioselective hydroarylation of styrenes with arylboronic acids using MeOH as the hydrogen source, providing an efficient method to access 1,1-diarylalkanes, which are essential structural units in many biologically active compounds. In addition, Ni-catalyzed enantioselective hydrovinylation of styrenes with vinylboronic acids is also realized with good yields and enantioselectivities. The synthetic utility was demonstrated by the efficient synthesis of (R)-(-)-ibuprofen.
Univ Chinese Acad Sci
2/27/2019Csp2_ar-Csp3-ring(s)Nu-NuBHB(OH)2HArylBenzylLiOEtIonic-ORNu-M_10.1038/s41467-019-12949-1,10.1038/s41467-019-11392-610.1021/acscatal.1c05732,10.1021/acs.oprd.1c00410,10.1002/cjoc.202100763,10.1021/acs.oprd.1c00410,10.1021/acs.orglett.1c04073,10.1039/d1cc05125c,10.6023/A21070338,10.1016/j.chempr.2021.10.015,10.1021/acscatal.1c04314,10.1038/s41467-021-26194-y,10.1002/chem.202102847,10.1002/anie.202109881,10.1055/a-1637-9308,10.1021/jacs.1c07851,10.1021/jacs.1c02220,10.1039/d1sc03121j,10.1021/acscatal.1c02299,10.1038/s41467-021-24094-9,10.1055/a-1523-3228,10.1002/anie.202105355,10.1021/acscatal.1c00908,10.1055/s-0040-1720406,10.1021/acs.organomet.1c00190,10.1021/jacs.1c02117,10.1021/acs.organomet.0c00819,10.1002/anie.202100137,10.1002/anie.202016268,10.1002/adsc.202100022,10.1021/acs.joc.0c02556,10.1038/s41467-020-20888-5,10.1007/s11426-020-9910-2,10.1002/anie.202012614,10.1021/acs.orglett.0c02898,10.1021/acs.orglett.0c03542,10.1021/jacs.0c10333,10.1021/acscatal.0c03884,10.1021/acs.orglett.0c03395,10.1021/acs.orglett.0c03416,10.1021/jacs.0c09125,10.1021/acscatal.0c03317,10.1002/anie.202011342,10.1021/acs.joc.0c01629,10.1002/anie.202010840,10.1002/anie.202010386,10.1021/acscatal.0c02959,10.1021/acs.joc.0c01509,10.1002/cjoc.202000376,10.1002/anie.202009195,10.1021/acscatal.0c02115,10.1021/acs.orglett.0c01607,10.1039/c9cc09450d,10.1039/d0cc02697b,10.1021/acs.orglett.0c01248,10.1002/anie.202004982,10.1002/ejoc.202000419,10.1021/acs.accounts.0c00032,10.1002/anie.202001069,10.6023/cjoc201911016,10.1002/anie.202001742,10.1039/d0qo00072h,10.1002/anie.201912753,10.1016/j.isci.2019.11.008,10.1016/j.trechm.2019.08.004,10.1021/acs.joc.9b02393,10.1002/anie.201912629,10.1038/s41467-019-12949-1,10.1021/jacs.9b07600,10.1016/j.trechm.2019.05.007,10.1002/ejoc.201900940,10.1002/anie.201907045,10.1038/s41467-019-11392-6,10.1021/acs.orglett.9b01120,10.1002/anie.2019010671/6/2022
222
235https://sci-hub.wf/https://doi.org/Ni784302017Morandi, B#N/ANickel-Catalyzed Cyanation of Aryl Chlorides and Triflates Using Butyronitrile: Merging Retro-hydrocyanation with Cross-Coupling
ANGEW CHEM INT EDIT
We describe a nickel-catalyzed cyanation reaction of aryl (pseudo)halides that employs butyronitrile as a cyanating reagent instead of highly toxic cyanide salts. A dual catalytic cycle merging retro-hydrocyanation and cross-coupling enables the conversion of a broad array of aryl chlorides and aryl/vinyl triflates into their corresponding nitriles. This new reaction provides a strategically distinct approach to the safe preparation of aryl cyanides, which are essential compounds in agrochemistry and medicinal chemistry.
Max Planck Inst Kohlenforsch
12/4/2017TRUETRUEFALSE_xxxx10.1021/acscatal.0c03993,10.1021/acs.joc.8b02498,10.1021/jacs.9b11208,10.1039/c8sc04437f10.1021/acs.joc.1c02098,10.1002/chem.202103700,10.1039/d1dt03331j,10.1002/hlca.202100200,10.1055/a-1675-0018,10.1055/a-1626-5749,10.1021/acs.orglett.1c02285,10.1055/a-1608-5693,10.1002/chem.202101273,10.1039/c9cs00571d,10.1002/anie.202103269,10.1021/acs.joc.1c00808,10.1039/d1cy00660f,10.1021/jacs.1c01923,10.1021/acs.orglett.1c00465,10.1039/d0cc07783f,10.1021/jacs.1c00529,10.1039/d0ob02518f,10.1039/d0dt03941a,10.1016/j.tetlet.2020.152749,10.1021/acs.joc.0c02346,10.1021/acs.chemrev.0c00301,10.1002/bkcs.12212,10.1021/acscatal.0c03993,10.1039/d0nj01996h,10.1055/s-0040-1705943,10.1016/j.tet.2020.131388,10.2533/chimia.2020.724,10.1038/s41467-020-17939-2,10.1002/anie.202005891,10.1016/j.jorganchem.2020.121337,10.1021/acs.orglett.0c01857,10.1021/jacs.0c03184,10.1039/d0cc01380c,10.1021/acs.organomet.0c00034,10.1055/s-0039-1691590,10.1021/acscatal.0c00980,10.1039/c9qo01402k,10.1021/acscatal.9b04586,10.1002/anie.201912803,10.1021/jacs.9b11208,10.1002/jcc.26099,10.1021/acscatal.9b02779,10.1021/acs.orglett.9b03170,10.1021/acs.joc.9b01692,10.1002/ejoc.201900909,10.1021/acs.orglett.9b02398,10.1021/acs.orglett.9b02797,10.1126/science.aaw3254,10.1002/anie.201803797,10.1002/anie.201903215,10.1021/acs.orglett.9b01941,10.1002/anie.201903890,10.1039/c9sc00640k,10.1021/jacs.9b03991,10.1055/s-0037-1611793,10.1002/hlca.201900059,10.1021/acscatal.8b05111,10.1039/c8ob02856g,10.1039/c8cc08930b,10.1039/c8sc04437f,10.1021/acs.orglett.8b03539,10.1021/acs.joc.8b02498,10.1021/acs.orglett.8b02854,10.1055/s-0037-1611062,10.1021/acs.orglett.8b02155,10.1021/jacs.8b06966,10.1021/jacs.8b06069,10.1021/jacs.8b06605,10.1007/s11426-018-9333-x,10.1039/c8ob01034j,10.1002/anie.201802563,10.1021/acs.joc.8b00515,10.1021/acs.orglett.8b00974Kelly#N/ADEC 42017FALSEFALSEFALSEFALSE564915693
223
198FALSEja307045r10.1021/ja307045rhttps://sci-hub.wf/10.1021/ja307045rhttps://doi.org/10.1021/ja307045rNiC-O ActivationKellyTRUE11214282012Shi, ZJ
Nickel-Catalyzed Enantioselective Cross-Couplings of Racemic Secondary Electrophiles That Bear an Oxygen Leaving Group
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
To date, effective nickel-catalyzed enantio-selective cross-couplings of alkyl electrophiles that bear oxygen leaving groups have been limited to reactions of allylic alcohol derivatives with Grignard reagents. In this Communication, we establish that, in the presence of a nickel/pybox catalyst, a variety of racernic propargylic carbonates are suitable partners for asymmetric couplings with organozinc reagents. The method is compatible with an array of functional groups and utilizes commercially available catalyst components. The development of a versatile nickel-catalyzed enantioselective cross-coupling process for electrophiles that bear a leaving group other than a halide adds a significant new dimension to the scope of these reactions.
Peking Univ9/12/2012TRUETRUEFALSECsp3-ring(s)-Csp2_arE-NuOMgOHMgXBenzylArylNo baseNo BaseStrong-0.81_10.1021/acs.joc.6b02564,10.1021/acscatal.7b02817,10.1021/ol4011757,10.1021/acs.orglett.8b03367,10.1021/acs.orglett.6b02656,10.1021/acscatal.1c05208,10.1021/acscatal.1c05208,10.1021/ja3089422,10.1021/acscatal.6b00801,10.1021/ol502682q,10.1021/acs.orglett.8b01062,10.1039/c7cc06106d,10.1021/jacs.0c12462,10.1021/ja413131m10.1021/acscatal.1c05338,10.1021/acscatal.1c05530,10.1021/acscatal.1c05208,10.1038/s41467-021-27437-8,10.1021/acscatal.1c04239,10.6023/cjoc202106021,10.1021/acs.joc.1c01790,10.1021/acscatal.1c02010,10.1039/c9cs00571d,10.1055/a-1467-2432,10.1039/d0cc08389e,10.1002/ejoc.202001602,10.1021/acs.orglett.0c04039,10.1021/acs.joc.0c02389,10.1021/jacs.0c12462,10.1055/s-0040-1705989,10.1039/d0sc04326e,10.1002/adsc.202000945,10.6023/A20070335,10.1055/s-0040-1707269,10.1021/acs.chemrev.9b00682,10.1002/cjoc.201900506,10.1021/jacs.0c02405,10.1002/ejoc.202000077,10.1039/d0cy00471e,10.1021/acs.joc.0c00008,10.1016/j.tetlet.2020.151729,10.1002/ajoc.201900758,10.1039/c9ob02328c,10.2174/1385272824666200211114540,10.1021/acs.joc.9b01851,10.1021/acs.orglett.9b03475,10.1021/acs.orglett.9b02946,10.1002/adsc.201900221,10.1021/acs.orglett.9b01669,10.1039/c9ob00628a,10.1021/acs.oprd.8b00325,10.1021/acs.orglett.8b03367,10.1039/c8ob02462f,10.1002/chem.201804415,10.1002/adsc.201801135,10.1021/acs.orglett.8b02434,10.1016/j.jorganchem.2018.04.036,10.1021/acs.orglett.8b01062,10.1039/c8ob00392k,10.1002/cjoc.201700664,10.1055/s-0036-1588568,10.1021/acs.orglett.7b03049,10.1021/acscatal.7b02817,10.1039/c7gc02540h,10.1002/cssc.201701287,10.1039/c7cc06106d,10.1021/jacs.7b06288,10.1016/j.tet.2017.03.058,10.1021/acs.joc.6b02564,10.1039/c6gc03355e,10.1016/j.cclet.2016.09.006,10.1021/acscatal.6b03277,10.1021/acs.orglett.6b02656,10.1002/ejoc.201600955,10.1021/acs.orglett.6b02459,10.1021/acscatal.6b01956,10.1021/acs.orglett.6b02274,10.1021/acscatal.6b00801,10.1021/acs.orglett.6b01134,10.1016/j.tet.2016.02.033,10.1016/bs.adomc.2016.07.001,10.1039/c6gc00163g,10.1039/c5qo00395d,10.1021/acscatal.5b02089,10.1021/acs.organomet.5b00710,10.1002/ejoc.201500987,10.1021/acs.orglett.5b01955,10.1007/s11426-015-5466-y,10.1021/acs.orglett.5b01466,10.1002/adsc.201400850,10.1021/cr500425u,10.1021/ar500345f,10.1021/ol503560e,10.1039/C5QO00243E,10.1039/c5ob00958h,10.1016/j.jcat.2014.10.013,10.1039/c4cc10084k,10.1021/ol502682q,10.1021/om500319h,10.1002/anie.201402576,10.1038/nature13274,10.1055/s-0033-1340665,10.1016/j.tet.2014.01.035,10.1515/pac-2014-5038,10.1016/j.inoche.2013.12.026,10.1021/ja413131m,10.1039/c4ra01341g,10.1021/cs400572q,10.1021/ja4076716,10.1021/ol4011757,10.3390/catal3020486,10.1021/ol400295z,10.1021/ja312087x,10.1021/ja3089422,10.1039/c3cc43616k,10.1039/c3ra44884c,10.1021/om300950c Long 11/9/2021SEP 122012FALSEFALSEFALSEFALSE1343614638
224
237FALSEcctc.20100022310.1002/cctc.201000223https://sci-hub.wf/10.1002/cctc.201000223https://doi.org/10.1002/cctc.201000223NiC-H ActivationGerryTRUE747#N/A2010Hirano, K
Oxidative Nickel-Air Catalysis in C-H Arylation: Direct Cross-Coupling of Azoles with Arylboronic Acids using Air as Sole Oxidant
CHEMCATCHEM
Osaka Univ11/1/2010yCsp2-Csp2_arNu-NuBHB(OH)2HVinylHetK3PO4Ionic-PO4Nu-M_xxx10.1021/ja306062c,10.1002/anie.201300459,10.1021/ja210249h,10.1039/c5sc02942b,10.1016/j.tet.2013.04.096,10.1002/chem.201101091,10.1021/ja413131m10.1080/00397911.2021.1949476,10.1002/tcr.202100113,10.1055/a-1335-7330,10.7536/PC200607,10.1016/j.chempr.2020.04.005,10.2174/1570178616666190705153927,10.1002/jsfa.10085,10.1021/acs.joc.9b02094,10.1016/j.tetlet.2019.151082,10.1002/ajoc.201900069,10.1021/acs.chemrev.8b00507,10.1007/s10562-018-2514-1,10.1055/s-0037-1609718,10.1039/c8qo00227d,10.1016/j.ica.2018.03.036,10.1002/ajoc.201800002,10.1039/c7ra13080e,10.1039/c7cc04252c,10.1002/cssc.201700321,10.1021/acs.joc.6b02675,10.1016/j.molcata.2016.11.009,10.1039/c6tc03003c,10.1002/anie.201606529,10.1007/s41061-016-0053-z,10.1002/slct.201600374,10.1021/acs.organomet.6b00003,10.1002/chem.201503926,10.1021/acs.orglett.5b02458,10.1055/s-0035-1560712,10.1021/acs.orglett.5b00510,10.1039/c5sc02942b,10.1039/c5dt00032g,10.1055/s-0034-1379073,10.1039/c4dt01547a,10.1021/ol502314p,10.1055/s-0034-1378325,10.1016/j.molcata.2014.03.017,10.1002/chem.201403356,10.1246/bcsj.20140099,10.1016/j.jorganchem.2013.12.055,10.1021/ol500531m,10.1055/s-0033-1340320,10.1021/ja413131m,10.1039/c3cy00503h,10.1039/c4ra06055e,10.1021/ja409803x,10.1016/j.tet.2013.04.096,10.1016/j.tet.2012.12.080,10.1039/c3gc41027g,10.1002/anie.201300459,10.1002/ejoc.201200914,10.1039/c3gc40753e,10.1016/j.tet.2012.05.091,10.1021/ja306062c,10.1021/ol301517y,10.1021/jo202663n,10.1002/ejoc.201200050,10.1021/ja210249h,10.1039/c2ob26270c,10.1002/anie.201106825,10.1039/c2cs35096c,10.3762/bjoc.7.187,10.1002/chem.201102644,10.1021/ja206850s,10.1002/chem.201101091,10.1002/chem.201100136,10.1021/ja111249p,10.1021/cr100379j,10.5059/yukigoseikyokaishi.69.252,10.1055/s-0030-125933212/29/2021
225
234FALSEja311783k10.1021/ja311783khttps://sci-hub.wf/10.1021/ja311783khttps://doi.org/10.1021/ja311783kNiC-O ActivationKellyTRUE19119322013Jarvo, ER
Direct Arylation/Alkylation/Magnesiation of Benzyl Alcohols in the Presence of Grignard Reagents via Ni-, Fe-, or Co-Catalyzed sp(3) C-O Bond Activation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Direct application of benzyl alcohols (or their magnesium salts) as electrophiles in various reactions with Grignard reagents has been developed via transition metal-catalyzed sp(3) C-O bond activation. Ni complex was found to be an efficient catalyst for the first direct cross coupling of benzyl alcohols with aryl/alkyl Grignard reagents, while Fe, Co, or Ni catalysts could promote the unprecedented conversion of benzyl alcohols to benzyl Grignard reagents in the presence of (n)hexylMgCl. These methods offer straightforward pathways to transform benzyl alcohols into a variety of functionalities.
Univ Calif Irvine3/6/2013TRUETRUETRUECsp3-ring(s)-Csp2_arE-NuOBOPivB(nep)BenzylArylKOtBuIonic-OtBuMedium0.33_xxxx10.1039/c7cc06717h,10.1021/jacs.7b04973,10.1002/anie.201308666,10.1021/ol5016724,10.1021/acs.orglett.8b01062,10.1021/jacs.6b11412,10.1039/c3cc46663a,10.1021/ja4034999,10.1021/ja408561b,10.1021/ja5026485,10.1021/jacs.6b08075,10.1021/jacs.9b00097,10.1038/s41467-019-11392-6,10.1021/acs.orglett.6b02656,10.1002/anie.201412051,10.1039/c5sc03704b,10.1021/ol502583h,10.1021/acscatal.7b02817,10.1021/jacs.1c0389810.6023/cjoc202106021,10.1021/acscatal.1c03980,10.1002/tcr.202100210,10.1039/d1sc03366b,10.1039/c9cs00571d,10.1021/jacs.1c03898,10.1021/acs.organomet.1c00085,10.1039/d0qo01607a,10.1021/acs.accounts.1c00050,10.1016/j.tetlet.2021.152947,10.1002/anie.202101682,10.1016/j.tetlet.2021.152862,10.1021/acs.orglett.0c04316,10.1021/acscatal.0c05484,10.1021/acs.orglett.0c04039,10.1007/s11426-020-9910-2,10.1055/s-0040-1705987,10.1016/j.tet.2020.131648,10.1055/s-0040-1707115,10.1021/acs.joc.0c00530,10.1002/ejoc.202000416,10.1002/aoc.5662,10.1007/s11426-019-9732-5,10.1039/d0cy00471e,10.1021/acs.joc.9b03433,10.1021/acsomega.9b04450,10.1016/j.tetlet.2020.151729,10.1002/chem.201904495,10.1039/c9qo01391a,10.1002/anie.201912739,10.1021/acs.orglett.9b03475,10.1002/asia.201900960,10.1021/acs.joc.9b01692,10.1016/j.jcat.2019.07.026,10.1021/acs.orglett.9b02308,10.1038/s41467-019-11392-6,10.1016/j.cclet.2019.04.008,10.1021/acs.orglett.9b01755,10.1002/ejoc.201900465,10.1021/acs.orglett.9b01669,10.1039/c9ob00628a,10.1016/j.ccr.2019.01.012,10.1021/jacs.9b00097,10.1038/s41467-019-09249-z,10.1002/adsc.201801446,10.1002/ejoc.201801494,10.1021/acs.oprd.8b00325,10.1002/adsc.201801135,10.1021/jacs.8b09909,10.1039/c8cc07093h,10.1021/acs.joc.8b01763,10.1002/anie.201806742,10.1021/acs.joc.8b00965,10.1039/c8ob01034j,10.1002/cctc.201800454,10.1002/anie.201712829,10.1016/j.jorganchem.2018.01.019,10.1021/acs.orglett.8b01062,10.1002/cctc.201701601,10.1002/adsc.201800150,10.1021/acs.orglett.8b00169,10.1002/chem.201705463,10.1055/s-0036-1591853,10.1016/j.tetlet.2017.11.049,10.1021/jacs.7b10855,10.1039/c7cc08416a,10.1039/c7cc06717h,10.1055/s-0036-1588572,10.1055/s-0036-1588563,10.1021/acscatal.7b02817,10.1055/s-0036-1590962,10.1016/j.tetlet.2017.09.022,10.1039/c7dt02532g,10.1021/jacs.7b04973,10.1021/acs.orglett.7b02076,10.1021/acs.orglett.7b02063,10.1021/acs.orglett.7b01510,10.1002/anie.201703380,10.1021/acscatal.7b00772,10.1002/anie.201703174,10.1021/jacs.7b03371,10.1021/acscatal.7b00300,10.1002/adsc.201601105,10.1002/adsc.201600814,10.1021/jacs.6b13299,10.1002/chem.201605445,10.1016/j.cclet.2016.09.006,10.1021/acscatal.6b03277,10.1021/jacs.6b11412,10.1002/anie.201609844,10.1021/acs.orglett.6b02656,10.1016/j.tetlet.2016.10.087,10.1021/acscatal.6b02392,10.1021/jacs.6b09533,10.1002/cjoc.201600330,10.1021/jacs.6b08075,10.1246/bcsj.20160135,10.1021/jacs.6b07396,10.1016/j.tet.2016.06.031,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1021/jacs.6b06285,10.1002/adsc.201600336,10.1002/adsc.201600590,10.1002/anie.201602075,10.1021/acs.orglett.6b00911,10.1055/s-0035-1561584,10.1021/acs.orglett.6b00744,10.1016/j.jorganchem.2016.02.005,10.1038/ncomms11065,10.3762/bjoc.12.49,10.1002/anie.201600305,10.1055/s-0035-1560960,10.1021/acssuschemeng.5b01282,10.1016/bs.adomc.2016.07.001,10.1039/c6ob01638c,10.1039/c6gc00163g,10.1039/c5cc10005d,10.1039/c5sc03704b,10.1021/acs.orglett.5b03455,10.1039/c6ra11116e,10.1002/anie.201505981,10.1002/chem.201504049,10.1002/chem.201503647,10.1021/jacs.5b09980,10.1002/anie.201505699,10.1002/anie.201505926,10.1021/acs.oprd.5b00148,10.1021/acs.chemrev.5b00162,10.1021/jacs.5b03870,10.1021/acscatal.5b00909,10.1021/acs.accounts.5b00223,10.1021/acs.joc.5b00991,10.1021/acs.orglett.5b01030,10.1021/jacs.5b03937,10.1021/jacs.5b03277,10.1016/j.tetlet.2015.02.121,10.1002/anie.201500396,10.1002/anie.201412051,10.1021/ol503607h,10.1021/jo502446k,10.1021/cs5014927,10.1021/ol503213z,10.1071/CH15459,10.1080/00397911.2015.1100746,10.1039/c4cc08559k,10.1039/c4cc10084k,10.1039/c4sc03106g,10.1016/S1872-2067(14)60217-5,10.1039/c4ra16452k,10.1021/cs501366q,10.1021/ol502583h,10.1002/chem.201404310,10.1016/j.tet.2014.03.039,10.1021/ol5016724,10.1021/jo5010636,10.1021/ja5039616,10.1021/ja5026485,10.1002/anie.201403046,10.1038/nature13274,10.1021/ja412159g,10.6023/cjoc201310035,10.1002/anie.201308666,10.1021/ol403680c,10.1021/ja412107b,10.1021/ja410883p,10.1002/anie.201307019,10.1039/c4cc05376a,10.1002/chem.201303683,10.1021/ja408561b,10.1002/chem.201302079,10.1016/j.tet.2013.05.001,10.1021/ja4034999,10.1021/ol400690t,10.1039/c3cc46663aKelly11/4/2021MAR 62013FALSEFALSEFALSEFALSE13593303
226
239FALSEacs.orglett.5b0221710.1021/acs.orglett.5b02217https://sci-hub.wf/10.1021/acs.orglett.5b02217https://doi.org/10.1021/acs.orglett.5b02217NiC-H ActivationGerry13-FebTRUE772#N/A2015Cai, C
Nickel-Catalyzed Regioselective Cross-Dehydrogenative Coupling of Inactive C(sp(3))-H Bonds with Indole DerivativesORG LETT
A nickel-catalyzed regiosepecific C2- versus C3-oxidative cross-coupling reaction of indoles with 1,4-dioxane and other inactive C(sp(3))-H bonds is described. The divergent synthesis of C(sp(3))-C(sp(2)) bonds was achieved in satisfactory yields with di-tert-butyl peroxide (DTBP) as the oxidant, which provides an efficient strategy for the selective construction of cyclic ethers containing heteroaromatic core structures.
Nanjing Univ Sci & Technol
10/2/2015Csp3-Csp2_arNu-NuHHHHAlkylHetNo baseNo BaseNu-H_xxx10.1021/acscatal.7b01044,10.1021/acs.orglett.6b0065810.1002/ajoc.202100726,10.1016/j.tet.2021.132610,10.1021/acs.joc.1c02346,10.1039/d1nj05749a,10.1021/acs.joc.1c02339,10.1039/d1gc03482k,10.1021/acscatal.1c03314,10.1021/acs.orglett.1c02440,10.1002/slct.202100339,10.1002/ajoc.202100006,10.6023/cjoc202004024,10.1016/j.tetlet.2020.152254,10.1021/jacs.0c05434,10.6023/cjoc202004028,10.1080/00397911.2020.1761394,10.1080/00397911.2020.1758143,10.1039/c9ob02653c,10.1016/j.tetlet.2019.151426,10.2174/1385272824999200616114037,10.1039/c9qo00926d,10.1039/c9ob01550g,10.1039/c9nj01728c,10.1016/j.tetlet.2019.05.016,10.1016/j.apcata.2019.04.020,10.1002/cctc.201900254,10.1021/acs.organomet.8b00888,10.1021/acs.orglett.9b00357,10.1021/acs.joc.8b03187,10.1039/c8cc08274j,10.1021/acs.orglett.8b02736,10.1039/c8qo00731d,10.1021/acs.orglett.8b02419,10.1021/acs.orglett.8b02453,10.1002/cctc.201800582,10.1016/j.jfluchem.2018.05.012,10.1016/j.tet.2018.05.045,10.1055/s-0037-1609445,10.1021/acs.orglett.8b00968,10.1039/c7ob02771k,10.1016/j.tetlet.2018.03.090,10.1039/c7qo01003f,10.1021/acssuschemeng.7b04213,10.2174/1570179415666180622102458,10.1002/ejoc.201701288,10.1016/j.tet.2017.10.046,10.1002/asia.201701258,10.6023/cjoc201704049,10.1002/ejoc.201700929,10.1002/slct.201701537,10.1039/c7sc01045a,10.1021/acs.orglett.7b02316,10.1002/cssc.201700783,10.1002/ejoc.201700341,10.1021/acscatal.7b01044,10.1021/acs.joc.7b00463,10.1002/ejoc.201700030,10.1039/c6sc05697k,10.1002/slct.201700263,10.1016/j.tetlet.2017.01.035,10.1039/c6cc09725a,10.1039/c7ob00022g,10.1039/c6cc08098g,10.1002/adsc.201600467,10.1016/j.tetlet.2016.11.018,10.1016/j.tet.2016.10.014,10.1016/j.molcata.2016.07.042,10.1021/acs.joc.6b00622,10.1055/s-0035-1561946,10.1002/asia.201600193,10.1055/s-0035-1561338,10.1021/acs.orglett.6b00658,10.1002/ajoc.201600037,10.1039/c6ob00076b,10.1016/bs.aihch.2016.04.005,10.1039/c6qo00369a1/5/2022
227
148FALSEjo982060h10.1021/jo982060hhttps://sci-hub.wf/10.1021/jo982060hhttps://doi.org/10.1021/jo982060hNiC-O ActivationLongTRUEx781#N/A1999Backvall, J
Nickel-Catalyzed Cross-Coupling of Dienyl Phosphates with Grignard Reagents in the Synthesis of 2-Substituted 1,3-DienesJ ORG CHEM#N/A#N/A2/1/1999Csp2-Csp3E-NuOMg
OPO(OPh)2
MgXVinylAlkylNo baseNo BaseStrong0.04_xxcannot find in web of scienceKelly1/4/2022
228
241FALSEacscatal.6b0112010.1021/acscatal.6b01120https://sci-hub.wf/10.1021/acscatal.6b01120https://doi.org/10.1021/acscatal.6b01120NiC-H ActivationElaine7-FebTRUE56532016
Ackermann, L
Nickel-Catalyzed C-H Alkynylation of Anilines: Expedient Access to Functionalized Indoles and Purine NucleobasesACS CATAL
C-H alkynylations of electron-rich anilines were accomplished by means of user-friendly nickel catalysis. The C-H functionalization occurred with high positional selectivity and ample scope by kinetically relevant C-H activation. The robust nickel catalyst tolerated synthetically useful functional groups, which set the stage for the facile synthesis of substituted indoles. The chemoselectivity of the cost-effective nickel catalyst was reflected by enabling transformative nickel-catalyzed C-H functionalization with purine nucleobases through monodentate chelation assistance.
Univ Gottingen7/1/2016TRUEFALSEFALSEYCsp1-Csp2_arE-NuHXHBrAlkyneArylLiOtBuIonic-OtBuNu-H_x10.1021/acscatal.6b02003,10.1002/anie.201709087,10.1021/acscatal.7b01044,10.1002/ajoc.201700569,10.1021/acs.orglett.6b0223610.1002/ajoc.202100772,10.1002/chem.202104107,10.1002/adsc.202100992,10.1002/adsc.202100823,10.1039/d1sc02937a,10.1002/adsc.202100305,10.1016/j.tetlet.2021.152872,10.1016/j.tetlet.2021.152869,10.1021/acs.orglett.0c04137,10.1021/acs.orglett.0c04068,10.1002/anie.202014877,10.1039/d0qo01120g,10.1021/acs.orglett.0c02609,10.1021/acscatal.0c01189,10.1021/acs.orglett.0c01126,10.1002/cjoc.201900468,10.1246/cl.200015,10.1039/c9ob02670c,10.1039/c9cc08735d,10.1021/acs.joc.9b02954,10.2174/1385272824999200616114037,10.1021/jacs.9b10868,10.1016/j.trechm.2019.06.002,10.1021/acscatal.9b02316,10.1039/c9ra03421h,10.1002/qua.25912,10.1039/c9cy00009g,10.1021/acs.chemrev.8b00507,10.1039/c8qo01215f,10.1002/anie.201813191,10.1039/c8cy01860j,10.1021/acscatal.8b03770,10.1002/slct.201802644,10.7536/PC180206,10.1039/c8cs00201k,10.1039/c8cc03445a,10.1021/acs.organomet.8b00177,10.1055/s-0037-1610142,10.1021/acs.orglett.8b01004,10.1002/asia.201800102,10.1002/adsc.201800161,10.1039/c8ob00585k,10.1021/acs.orglett.8b00772,10.1039/c7cc09308j,10.1002/ajoc.201700569,10.1002/anie.201709087,10.1039/c7ob01899a,10.1021/acs.orglett.7b02823,10.1039/c7cc05532c,10.1039/c7ob01791j,10.1021/acs.orglett.7b02247,10.1002/ejoc.201700788,10.1039/c7cc05011a,10.1002/chem.201605657,10.1021/acs.orglett.7b01294,10.1021/acscatal.7b01044,10.1002/cssc.201700321,10.1002/anie.201611118,10.1002/chem.201700587,10.1002/anie.201611595,10.1021/acscatal.6b03236,10.1002/anie.201609014,10.1002/chem.201606026,10.1002/chem.201605306,10.1007/s40010-016-0289-6,10.1021/acscatal.6b02477,10.1021/acs.orglett.6b02549,10.1002/anie.201606529,10.1021/acs.orglett.6b02236,10.1021/acs.orglett.6b02199,10.1002/chem.201603092,10.1021/acscatal.6b02003,10.1007/s41061-016-0053-z,10.1039/c6ob01856d11/6/2021JUL2016FALSEFALSEFALSEFALSE674690
229
179FALSEja403499910.1021/ja4034999https://sci-hub.wf/10.1021/ja4034999https://doi.org/10.1021/ja4034999NiC-O ActivationKellyTRUE9719322013Jarvo, ER
Retention or Inversion in Stereospecific Nickel-Catalyzed Cross-Coupling of Benzylic Carbamates with Arylboronic Esters: Control of Absolute Stereochemistry with an Achiral Catalyst
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Stereospecific coupling of benzylic carbamates and pivalates with aryl- and heteroarylboronic esters has been developed. The reaction proceeds with selective inversion or retention at the electrophilic carbon, depending on the nature of the ligand. Tricyclohexylphosphine ligand provides the product with retention, while an N-heterocyclic carbene ligand provides the product with inversion.
Univ Calif Irvine6/19/2013TRUETRUEFALSEyCsp3-ring(s)-Csp3E-NuOZn
(Methylthio)acetic
Zn(Me)2
BenzylAlkylNo baseNo BaseMedium0.31_x10.1021/ol502583h,10.1021/ja5029793,10.1002/anie.201511486,10.1021/ja5026485,10.1021/jacs.1c03898,10.1039/c8sc00609a,10.1021/acs.orglett.6b00819,10.1021/jacs.6b08075,10.1002/anie.201412051,10.1021/jacs.7b04973,10.1002/chem.201603436,10.1021/ol502682q,10.1021/acscatal.8b03436,10.1021/jacs.9b00097,10.1002/anie.201308666,10.1002/ejic.201900692,10.1002/anie.201507494,10.1021/ja5076426,10.1039/c7cc06106d10.1002/anie.202117843,10.1002/anie.202113836,10.6023/cjoc202106021,10.1016/j.jorganchem.2021.122068,10.1021/acs.orglett.1c02458,10.1021/acs.inorgchem.1c01720,10.1021/jacs.1c03898,10.1039/d1sc01217g,10.1016/j.tetlet.2021.152947,10.1002/anie.202101682,10.1002/anie.202014080,10.1021/acs.joc.0c02556,10.1055/s-0040-1706013,10.1055/s-0040-1705987,10.1039/d0ra09110c,10.1038/s41586-020-2399-1,10.1021/acs.chemrev.9b00682,10.1007/s11426-019-9732-5,10.1021/acs.orglett.9b03475,10.1002/ejic.201900692,10.1039/c9ob00628a,10.1021/jacs.9b00097,10.1002/chem.201803642,10.1055/s-0037-1610410,10.1002/anie.201811343,10.1016/j.bmcl.2018.12.011,10.1021/acs.organomet.8b00720,10.1021/acscatal.8b03436,10.1039/c8cc07093h,10.1021/acs.joc.8b01763,10.1021/jacs.8b05143,10.1021/acs.joc.8b01547,10.1002/anie.201806742,10.1016/j.jorganchem.2018.01.019,10.1039/c8sc00609a,10.1002/cctc.201701601,10.1021/acs.joc.8b00027,10.1021/acs.orglett.8b00169,10.1002/cjoc.201700664,10.1002/chem.201705463,10.1021/acs.joc.7b02780,10.1002/anie.201708748,10.1002/anie.201709411,10.3762/bjoc.13.228,10.1021/jacs.7b04973,10.1039/c7cc06106d,10.1021/jacs.7b07983,10.1002/anie.201703380,10.1021/acs.orglett.7b01022,10.1021/jacs.7b01705,10.1002/anie.201611720,10.1021/acs.joc.6b02586,10.1002/chem.201603436,10.1021/acscatal.6b01956,10.1021/acscatal.6b02124,10.1021/jacs.6b08075,10.1002/adsc.201600590,10.1002/anie.201602075,10.1021/acs.orglett.6b00819,10.1002/anie.201511486,10.1002/anie.201507494,10.1016/bs.adomc.2016.07.001,10.1039/c6sc01086e,10.1039/c6gc00163g,10.1002/chem.201503647,10.1021/jacs.5b08103,10.1021/acs.oprd.5b00148,10.1021/acs.chemrev.5b00162,10.1021/acs.accounts.5b00223,10.1021/jacs.5b03955,10.1002/anie.201412051,10.1021/ar500345f,10.1021/ol503607h,10.1021/ja510980d,10.1039/c4cc10084k,10.1039/c4sc03106g,10.1021/ol502583h,10.1021/ol502682q,10.1021/ja5076426,10.1021/ja505776m,10.1016/j.tet.2014.03.039,10.1002/anie.201309074,10.1002/chem.201402509,10.1021/jo5010636,10.1021/ja5026485,10.1021/ja5029793,10.1021/om5001327,10.1515/pac-2014-5041,10.1002/anie.201308666,10.1021/ja412107b,10.1021/ja410883p,10.1021/ol4023358Kelly11/5/2021JUN 192013FALSEFALSEFALSEFALSE135249083
230
305FALSEja408561b10.1021/ja408561bhttps://sci-hub.wf/10.1021/ja408561bhttps://doi.org/10.1021/ja408561bNiC-O ActivationJustin23-JunTRUE1471972013Fu, GC
Functional-Group-Tolerant, Nickel-Catalyzed Cross-Coupling Reaction for Enantioselective Construction of Tertiary Methyl-Bearing Stereocenters
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
The first Negishi nickel-catalyzed stereospecific cross-coupling reaction of secondary benzylic esters is reported. A series of traceless directing groups is evaluated for ability to promote cross-coupling with dimethylzinc. Esters with a chelating thioether derived from commercially available 2-(methylthio)acetic acid are most effective. The products are formed in high yield and with excellent stereospecificity. A variety of functional groups are tolerated in the reaction including alkenes, alkynes, esters, amines, imides, and O-, S-, and N-heterocycles. The utility of this transformation is highlighted in the enantioselective synthesis of a retinoic acid receptor agonist and a fatty acid amide hydrolase inhibitor.
10/28/2013Csp3-Csp2_arE-NuOZnOHZnXAlkylArylNo baseNo BaseStrong-0.816/29/2022
231
182FALSEja410704d10.1021/ja410704dhttps://sci-hub.wf/10.1021/ja410704dhttps://doi.org/10.1021/ja410704dNiC-O ActivationLongTRUE11112382014Weix, DJ
Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
A tertiary stereogenic center that bears two different aryl substituents is found in a variety of bioactive compounds, including medicines such as Zoloft and Detrol. We have developed an efficient method for the synthesis of enantioenriched 1,1-diarylalkanes from readily available racemic benzylic alcohols. Formation of a benzylic mesylate (which is not isolated), followed by treatment with an arylzinc reagent, LiI, and a chiral nickel/bis(oxazoline) catalyst, furnishes the Negishi cross-coupling product in high ee and good yield. A wide array of functional groups (e.g., an aryl iodide, a thiophene, and an N-Boc-indole) are compatible with the mild reaction conditions. This method has been applied to a gram-scale synthesis of a precursor to Zoloft.
Univ Rochester1/8/2014TRUETRUEFALSEyyCsp2_ar-Csp3E-EOX
O(Ring-Opening)
BrArylAlkylpyridineNitrogenNitrogen(neutral)Weak1_10.1039/c8sc00609a,10.1002/chem.201601320,10.1021/jacs.0c13093,10.1021/jacs.7b03448,10.1039/c9sc03347e,10.1002/anie.201503936,10.1021/jacs.5b01909,10.1039/c7sc03140h,10.1021/acs.orglett.7b00831,10.1021/ol502682q,10.1021/acs.orglett.8b03367,10.1021/ja510653n10.1002/anie.202201370,10.1039/d2ra00010e,10.1055/s-0041-1737762,10.1021/jacs.1c11170,10.1016/j.chempr.2021.10.023,10.1021/acs.jpca.1c07707,10.6023/cjoc202106021,10.1021/acscatal.1c04143,10.1016/j.tetlet.2021.153369,10.1021/jacs.1c08105,10.1039/c9cs00571d,10.1021/jacs.1c00659,10.3389/fchem.2021.613633,10.3390/polym13060987,10.1021/jacs.0c13093,10.1021/acssuschemeng.0c08262,10.1021/acs.joc.0c01233,10.1021/acs.orglett.0c03865,10.1021/acs.chemrev.0c00245,10.1021/acscatal.0c03237,10.1002/ejoc.202000966,10.1021/acscatal.0c01842,10.1039/d0sc01462a,10.1021/jacs.0c02673,10.1021/acscatal.0c01199,10.1021/acs.orglett.0c00960,10.1021/jacs.0c01724,10.1002/anie.201903726,10.1002/chem.201905048,10.1021/acs.joc.9b02465,10.1021/acs.orglett.9b03102,10.1039/c9sc03347e,10.1021/acs.orglett.9b02221,10.1021/acs.orglett.9b01987,10.1021/jacs.9b04993,10.1039/c8ob02141d,10.1021/acs.biomac.8b01608,10.1021/acs.organomet.8b00720,10.1021/acs.orglett.8b03367,10.1021/acscatal.8b03930,10.1021/jacs.8b09473,10.1021/jacs.8b06458,10.1021/acscatal.8b02029,10.1002/anie.201803228,10.1039/c8sc00609a,10.1021/acscatal.8b00244,10.1021/jacs.7b12212,10.1039/c7np00065k,10.1039/c7sc03140h,10.1002/ejlt.201700133,10.1055/s-0036-1589102,10.1002/cjoc.201700071,10.1021/acs.orglett.7b02076,10.1021/acs.orglett.7b00831,10.1021/jacs.7b03448,10.1039/c7cc01655g,10.1016/j.jorganchem.2017.01.009,10.1021/acs.orglett.6b03430,10.1039/c6cc07924e,10.1021/acs.orglett.6b03090,10.1021/acs.orglett.6b02862,10.1021/jacs.6b08507,10.1002/tcr.201600039,10.1021/acs.orglett.6b01675,10.1002/chem.201602486,10.1021/acs.orglett.6b01134,10.1002/chem.201601320,10.1021/jacs.6b01533,10.1038/ncomms11129,10.1016/bs.aihch.2016.04.002,10.1039/c5cc09817c,10.1039/c6cc04410g,10.1021/acs.orglett.5b02716,10.1134/S1070428015110019,10.1002/anie.201503936,10.1021/jacs.5b03870,10.1021/acs.accounts.5b00057,10.1021/jacs.5b03428,10.1021/jacs.5b01909,10.1039/c4cc09321f,10.1039/c4sc03106g,10.1039/c5qo00224a,10.1021/ja509077a,10.1021/ja512040c,10.1021/ja510653n,10.1002/chem.201405223,10.1002/chem.201405296,10.1021/ol502682q,10.1021/om5004682,10.1021/cr500036t,10.1021/jo500507s,10.1080/00397911.2014.924141,10.1039/c4qo00012aKelly11/16/2021JAN 82014FALSEFALSEFALSEFALSE136148
232
161FALSEja502648510.1021/ja5026485https://sci-hub.wf/10.1021/ja5026485https://doi.org/10.1021/ja5026485NiC-O ActivationLongTRUE8510322014Jarvo, ER
Nickel-Catalyzed Regiodivergent Opening of Epoxides with Aryl Halides: Co-Catalysis Controls Regioselectivity
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Epoxides are versatile intermediates in organic synthesis, but have rarely been employed in cross-coupling reactions. We report that bipyridine-ligated nickel can mediate the addition of functionalized aryl halides, a vinyl halide, and a vinyl triflate to epoxides under reducing conditions. For terminal epoxides, the regioselectivity of the reaction depends upon the cocatalyst employed. Iodide cocatalysis results in opening at the less hindered position via an iodohydrin intermediate. Titanocene cocatalysis results in opening at the more hindered position, presumably via Ti-III-mediated radical generation. 1,2-Disubstituted epoxides are opened under both conditions to form predominantly the trans product.
Univ Calif Irvine6/4/2014TRUETRUEFALSEIntramolecular cyclizationCsp2_ar-Csp2E-NuOHOMeHArylVinylNo baseNo BaseStrong-0.28_10.1021/ja5076426,10.1021/ol502583h,10.1021/jacs.7b04973,10.1021/acs.orglett.6b02656,10.1021/jacs.9b00097,10.1021/jacs.6b03253,10.1021/jacs.7b02326,10.1002/anie.201810757,10.1002/anie.202011036,10.1039/d1cc00634g10.1039/d1cc05949a,10.1021/acs.joc.1c00858,10.1021/acs.joc.1c00983,10.1016/j.tetlet.2021.152947,10.1021/jacs.1c00618,10.1039/d1cc00634g,10.1021/acs.joc.0c02605,10.1021/acs.orglett.0c03998,10.1002/anie.202011036,10.1021/acs.orglett.0c03146,10.1055/s-0040-1705966,10.1002/adsc.202000820,10.1002/ejoc.202000672,10.1002/anie.202004177,10.1002/slct.202000814,10.1021/acs.orglett.0c00900,10.1021/acs.orglett.0c00945,10.1055/s-0039-1690718,10.1039/c9cc09497k,10.1002/adsc.201901398,10.1021/acs.orglett.9b03475,10.1016/j.tetlet.2019.150955,10.1021/acs.orglett.9b02577,10.1021/jacs.9b00097,10.1055/s-0037-1611659,10.1002/anie.201810757,10.1021/jacs.8b10874,10.1002/ajoc.201800535,10.1021/jacs.8b09401,10.1021/acs.joc.8b02279,10.1039/c8cc07093h,10.1021/jacs.8b06966,10.1021/jacs.8b05374,10.1021/jacs.8b03163,10.1016/j.jorganchem.2018.01.019,10.1002/ejoc.201800155,10.1021/acs.organomet.7b00812,10.1039/c7sc04351a,10.1021/jacs.7b06185,10.1055/s-0036-1590962,10.1021/acs.orglett.7b02867,10.1002/anie.201707134,10.1021/jacs.7b04973,10.1002/anie.201704119,10.1021/jacs.7b06340,10.1021/acs.orglett.7b01054,10.1021/jacs.7b03371,10.1021/jacs.7b02326,10.1038/s41570-017-0025,10.1021/acs.orglett.6b02656,10.1002/chem.201604061,10.1021/acs.organomet.6b00532,10.1021/jacs.6b08486,10.1021/jacs.6b03253,10.1002/anie.201600697,10.1016/j.tet.2016.01.004,10.1002/adsc.201500822,10.1021/acssuschemeng.5b01282,10.1016/bs.adomc.2016.07.001,10.1039/c6gc00163g,10.1039/c5cc10005d,10.1039/c6ra07130a,10.1021/acs.orglett.5b02482,10.1016/j.tet.2015.04.066,10.1021/jacs.5b03870,10.1002/anie.201503641,10.1002/anie.201503204,10.1002/ajoc.201500148,10.1039/c4cy01331j,10.1039/c5sc00505a,10.1039/c4cc10084k,10.1016/S1872-2067(14)60217-5,10.1021/ol502583h,10.1021/ja5076426,10.1021/ja5066015,10.1039/c4ra08421g,10.1039/c4cs00206g,10.1039/c4ra08517eKelly2/7/2022JUN 42014FALSEFALSEFALSEFALSE136227825
233
207FALSEja502979310.1021/ja5029793https://sci-hub.wf/10.1021/ja5029793https://doi.org/10.1021/ja5029793NiC-O Activation8-FebTRUE12115182014Martin, R
Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Enantioenriched methylenecyclopentanes are synthesized by stereospecific, nickel-catalyzed Heck cyclizations of secondary benzylic ethers. The reaction proceeds in high yield and enantiospecificity for benzylic ethers of both pi-extended and simple arenes. Ethers with pendant 1,2-disubstituted olefins form trisubstituted olefins with control of both absolute configuration and alkene geometry. Diastereoselective synthesis of a polycyclic furan is demonstrated.
Inst Chem Res Catalonia ICIQ
5/21/2014Csp2_ar-Csp2E-NuOHOTsHAryl
Carbonyl
No baseNo BaseWeak0.36_10.1021/acs.orglett.6b02656,10.1002/anie.201412051,10.1002/anie.201805611,10.1021/acscatal.7b00941,10.1021/acs.orglett.6b02265,10.1039/c7sc03140h,10.1021/acs.orglett.7b00556,10.1038/s41929-020-00560-3,10.1021/acscatal.6b00801,10.1039/c8sc00609a,10.1038/ncomms14878,10.1021/jacs.9b05224,10.1021/acscatal.0c03993,10.1021/jacs.1c09797,10.1021/acscatal.7b0105810.1039/d1ra08771a,10.1016/j.tet.2021.132526,10.1021/jacs.1c09797,10.1021/acs.accounts.1c00480,10.1021/acscatal.1c02952,10.1246/cl.210333,10.1021/acs.orglett.1c02223,10.1021/acscatal.1c02913,10.1021/acs.orglett.1c00313,10.1038/s41929-020-00560-3,10.1039/d0sc06056a,10.1055/a-1349-3543,10.1038/s41467-020-19944-x,10.1021/acscatal.0c03993,10.1016/j.cej.2020.125788,10.1021/acs.chemrev.0c00088,10.1002/cctc.202000876,10.1021/acs.chemrev.9b00682,10.1039/d0sc01349h,10.1021/jacs.0c00283,10.1021/acs.joc.9b03500,10.1002/ejoc.201901883,10.1002/anie.202000224,10.1039/c9cc08727c,10.1021/jacs.9b12297,10.1021/acs.orglett.9b03170,10.1021/acscatal.9b02641,10.1021/jacs.9b05224,10.1021/acs.orglett.9b00692,10.1002/chem.201806239,10.1039/c8cc09913h,10.1039/c8ob02312c,10.1021/acs.organomet.8b00747,10.1007/3418_2018_19,10.1039/c8qo01044g,10.1021/acscatal.8b03930,10.1021/acs.joc.8b02104,10.1002/cctc.201800898,10.1021/acscatal.8b02784,10.1002/anie.201807393,10.1002/adsc.201800729,10.1002/anie.201805611,10.1039/c8sc00742j,10.1002/ejoc.201800175,10.1016/j.tetlet.2018.04.076,10.1039/c8cc02499e,10.1002/chem.201801241,10.1039/c8sc00609a,10.1021/acs.orglett.8b00496,10.1002/aoc.4284,10.1002/cjoc.201700664,10.1021/acs.joc.7b02740,10.1021/acs.orglett.7b03713,10.1055/s-0036-1591853,10.1039/c7sc03140h,10.1039/c7sc03950f,10.1021/acs.orglett.7b03669,10.1055/s-0036-1588568,10.1055/s-0036-1590962,10.1021/acs.joc.7b01468,10.1021/acscatal.7b02795,10.1039/c7cc06881f,10.1021/acs.orglett.7b02821,10.1039/c7dt02532g,10.1039/c7sc02578e,10.1055/s-0036-1588464,10.1021/acscatal.7b00941,10.1021/acscatal.7b01058,10.1021/acs.orglett.7b00885,10.1021/acs.joc.6b02701,10.1021/acs.orglett.7b00556,10.1038/ncomms14878,10.6023/cjoc201610009,10.1002/anie.201611720,10.1021/acs.joc.6b02693,10.1021/jacs.6b10998,10.1021/acscatal.6b03040,10.1016/j.tet.2016.10.059,10.1002/anie.201607959,10.1021/jacs.6b10351,10.1021/acs.orglett.6b02656,10.1021/acscatal.6b01687,10.1002/chem.201604061,10.1021/acs.chemrev.6b00237,10.1021/acscatal.6b01956,10.1002/anie.201605162,10.1021/acs.orglett.6b02265,10.1007/s41061-016-0043-1,10.1007/s41061-016-0042-2,10.6023/cjoc201602007,10.1021/acscatal.6b00801,10.1002/tcr.201500250,10.1021/acs.orglett.6b00195,10.1002/ejoc.201501349,10.1016/bs.adomc.2016.07.001,10.1039/c5qo00395d,10.1039/c5cc10005d,10.1021/acs.joc.5b02557,10.1021/acs.orglett.5b03061,10.1002/anie.201506751,10.1021/acscatal.5b02165,10.1021/jacs.5b08103,10.1007/s11426-015-5364-3,10.1021/acs.orglett.5b01229,10.1021/acs.orglett.5b01283,10.1021/jacs.5b03955,10.1021/acs.accounts.5b00051,10.1016/j.tetlet.2015.04.069,10.1021/acscatal.5b00306,10.1002/adsc.201400970,10.1002/anie.201412051,10.1039/c5nj00655d,10.1039/c4cc10084k,10.1002/chem.201405296,10.1002/chem.201402509,10.1039/c4cs00206gKelly2/17/2022
234
126FALSEja507642610.1021/ja5076426https://sci-hub.wf/10.1021/ja5076426https://doi.org/10.1021/ja5076426NiC-O ActivationShihongTRUE6210322014Jarvo, ER
Ni-Catalyzed Direct Reductive Amidation via C-O Bond Cleavage
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
A novel Ni-catalyzed reductive amidation of C(sp(2))-O and C(sp(3))-O electrophiles with isocyanates is described. This umpolung reaction allows for an unconventional preparation of benzamides using simple starting materials and easy-to-handle Ni catalysts.
Univ Calif Irvine10/22/2014TRUEFALSEFALSECsp3-Csp3E-NuOMg
O(Ring-Opening)
MgXAlkylAlkylNo baseNo BaseWeak1_ring open10.1021/jacs.7b02326,10.1021/acs.orglett.6b02656,10.1039/c8sc00609a,10.1021/jacs.1c03898,10.1002/anie.201412051,10.1021/jacs.0c01330,10.1021/jacs.7b04973,10.1021/acs.orglett.6b00819,10.1002/chem.201603436,10.1021/jacs.9b0009710.6023/cjoc202106021,10.3390/molecules26195947,10.1021/acs.orglett.1c02458,10.1021/acs.inorgchem.1c01720,10.1021/jacs.1c03898,10.1021/acs.accounts.1c00050,10.1016/j.ica.2021.120300,10.1016/j.tetlet.2021.152947,10.1055/s-0040-1705987,10.1021/acs.chemrev.9b00682,10.1021/jacs.0c01330,10.1055/s-0039-1690718,10.1002/chem.202000215,10.1021/acs.orglett.9b03475,10.1016/j.tetlet.2019.150955,10.1021/acscatal.9b02636,10.1002/ijch.201900071,10.1039/c9ob00628a,10.1021/jacs.9b00097,10.1007/s00706-019-2364-6,10.1002/chem.201803642,10.1039/c8cc07093h,10.1021/acs.organomet.8b00438,10.1016/j.jorganchem.2018.01.019,10.1039/c8sc00609a,10.1021/acs.joc.8b00027,10.1021/acs.orglett.8b00319,10.1002/cjoc.201700664,10.1002/chem.201705463,10.1021/jacs.7b08326,10.1055/s-0036-1590962,10.1021/jacs.7b04973,10.1002/anie.201704119,10.1002/anie.201703380,10.1021/jacs.7b02326,10.1021/acs.joc.7b00419,10.1038/s41570-017-0025,10.1002/chem.201606046,10.1021/acs.orglett.6b02656,10.1021/jacs.6b07567,10.1002/chem.201603436,10.1002/adsc.201600492,10.1021/acs.orglett.6b01745,10.1002/adsc.201600590,10.1021/jacs.6b03384,10.1021/acs.orglett.6b00819,10.1021/acscatal.5b02718,10.1055/s-0035-1560960,10.1016/j.tetasy.2015.11.009,10.1016/bs.adomc.2016.07.001,10.1021/acs.oprd.5b00148,10.1021/acs.chemrev.5b00162,10.1016/j.tet.2015.04.066,10.1021/jacs.5b03870,10.1021/acs.accounts.5b00223,10.1002/anie.201412051,10.1021/ol503607h,10.1039/c5cc02884aKelly11/25/2021OCT 222014FALSEFALSEFALSEFALSE1364214951
235
229FALSEja510653n10.1021/ja510653nhttps://sci-hub.wf/10.1021/ja510653nhttps://doi.org/10.1021/ja510653nNiC-O ActivationShihongTRUE1811412014Gong, HG
Stereospecific Cross-Coupling Reactions of Aryl-Substituted Tetrahydrofurans, Tetrahydropyrans, and Lactones
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
The stereospecific ring-opening of O-heterocycles to provide acyclic alcohols and carboxylic acids with controlled formation of a new CC bond is reported. These reactions provide new methods for synthesis of acyclic polyketide analogs with complex stereochemical arrays. Stereoselective synthesis of the cyclic template is utilized to control relative configuration; subsequent stereospecific nickel-catalyzed ring-opening affords the acyclic product. Aryl-substituted tetrahydrofurans and tetrahydropyrans undergo nickel-catalyzed Kumada-type coupling with a range of Grignard reagents to furnish acyclic alcohols with high diastereoselectivity. Enantioenriched lactones undergo Negishi-type cross-coupling with dimethylzinc to afford enantioenriched carboxylic acids. Application in a two-step enantioselective synthesis of an anti-dyslipidemia agent is demonstrated.
Shanghai Univ12/17/2014TRUETRUETRUECsp2-Csp3E-EOXOHBr
Carbonyl
AlkyliPr2NEtNitrogenNitrogen(neutral)Strong-0.81_xx10.1021/jacs.8b12801,10.1021/acs.orglett.9b01014,10.1021/acs.joc.5b00135,10.1021/acscatal.9b00521,10.1002/anie.202002271,10.1039/c5cc03113c,10.1021/acscatal.0c00246,10.1002/anie.201705521,10.1039/c7sc03140h,10.1039/d0sc05452f,10.1039/c9sc03347e,10.1021/acs.orglett.9b01164,10.1039/c8sc00609a,10.1246/bcsj.2014038710.1002/adsc.202200003,10.1002/ajoc.202100665,10.1039/d2ra00010e,10.1055/s-0041-1737762,10.1080/07328303.2021.2015366,10.1021/jacs.1c10932,10.1021/jacs.1c11170,10.1002/anie.202114731,10.1021/acs.orglett.1c03390,10.1039/d1qo01219c,10.1021/acscatal.1c02307,10.1021/acscatal.1c03265,10.1021/jacs.1c07851,10.1002/anie.202106273,10.1038/s41467-021-25127-z,10.1002/anie.202104430,10.1021/jacs.1c05567,10.1039/d1sc03596g,10.1021/acscatal.1c02088,10.1021/acs.orglett.1c01713,10.1002/adsc.202100596,10.1038/s41467-021-23887-2,10.6023/cjoc202010027,10.1039/d1qo00264c,10.1016/j.mencom.2021.03.043,10.1021/jacs.1c02629,10.1039/d0cs01107j,10.1021/acs.orglett.1c00431,10.1021/acs.orglett.1c00551,10.1021/acs.orglett.1c00313,10.1039/d0sc06446g,10.1016/j.tet.2021.131955,10.1007/s11426-020-9930-7,10.1021/acs.orglett.1c00058,10.1002/cjoc.202000500,10.1002/anie.202014660,10.1039/d0sc05452f,10.1021/acs.orglett.0c03342,10.1055/a-1328-0352,10.1021/jacs.0c10471,10.1021/acscatal.0c03237,10.1038/s41467-020-19194-x,10.1021/jacs.0c08708,10.1002/adsc.202000985,10.1007/s11426-020-9838-x,10.1021/acs.accounts.0c00291,10.1021/jacs.0c07634,10.1021/jacs.0c06882,10.6023/cjoc202003037,10.1039/d0ob00711k,10.1021/acs.orglett.0c01612,10.1038/s41467-020-17224-2,10.1021/jacs.0c03298,10.1002/anie.202002271,10.1021/jacs.0c02673,10.1021/jacs.0c02839,10.1021/acs.orglett.0c00554,10.1021/acs.organomet.0c00082,10.1021/acscatal.0c00246,10.1021/acs.orglett.0c00561,10.1002/anie.201914221,10.1038/s41467-019-14016-1,10.1021/acs.joc.9b02431,10.1002/asia.201901490,10.1039/c9sc03672e,10.1021/jacs.9b10026,10.1039/c9sc03347e,10.1021/acs.orglett.9b02779,10.1021/acscatal.9b03172,10.1055/s-0039-1690158,10.1002/chem.201903668,10.1002/ejoc.201901037,10.1021/acs.orglett.9b02788,10.1002/ijch.201900072,10.1021/acscatal.9b02081,10.1246/cl.190405,10.1002/anie.201906000,10.1002/ejoc.201900850,10.1002/med.21625,10.1039/c9cy00938h,10.1002/anie.201903330,10.1039/c9cc00768g,10.1021/acs.orglett.9b01164,10.1002/anie.201901927,10.1039/c9cc01047e,10.1021/acs.orglett.9b01097,10.1021/jacs.9b02238,10.1021/acs.orglett.9b00692,10.1021/acs.orglett.9b01014,10.1021/acscatal.9b00336,10.1021/acscatal.9b00521,10.1002/anie.201900995,10.6023/cjoc201806038,10.1002/chem.201805682,10.1021/jacs.8b12801,10.1021/acs.organomet.8b00720,10.1021/acscentsci.8b00628,10.1021/acs.orglett.8b03567,10.1039/c8qo01044g,10.1021/acs.orglett.8b03539,10.1021/acscatal.8b03930,10.1038/s41467-018-07069-1,10.1021/jacs.8b09473,10.1021/acscatal.8b02784,10.1021/acs.organomet.8b00244,10.1038/s41467-018-04646-2,10.1002/anie.201800701,10.1039/c8sc00609a,10.1021/acs.orglett.8b01117,10.1021/acs.joc.8b00340,10.1021/acs.orglett.8b00413,10.1021/acs.orglett.8b00408,10.1039/c8cc00001h,10.1055/s-0036-1591853,10.1021/jacs.7b12582,10.1039/c7sc03140h,10.1021/acscatal.7b03388,10.1039/c7qo00716g,10.1016/bs.aihch.2017.10.001,10.1039/c7cc07055a,10.1021/acs.chemrev.7b00234,10.1002/anie.201705521,10.1002/anie.201706781,10.1002/cjoc.201700071,10.1002/anie.201705520,10.1021/acs.orglett.7b01588,10.6023/cjoc201703042,10.1039/c7sc01170a,10.6023/cjoc201612031,10.1002/anie.201702857,10.1021/acs.orglett.7b01128,10.1021/jacs.6b12653,10.1055/s-0036-1588132,10.6023/cjoc201610009,10.1016/j.tetlet.2016.12.013,10.1021/acs.orglett.6b03158,10.1021/acs.orglett.6b02665,10.1002/anie.201605162,10.1055/s-0035-1562442,10.1021/jacs.6b05788,10.1002/chem.201602486,10.1007/s41061-016-0042-2,10.6023/cjoc201602007,10.1021/jacs.6604088,10.1021/jacs.6b03897,10.1021/jacs.6b01533,10.1002/anie.201600697,10.1021/acs.joc.5b02853,10.1002/anie.201511438,10.1021/acs.orglett.5b03591,10.1002/ejoc.201501349,10.1039/c5ob02094h,10.1055/s-0035-1560531,10.1021/jacs.5b08304,10.1021/jacs.5b06255,10.1016/j.tetlet.2015.05.117,10.1021/acs.accounts.5b00057,10.1021/jacs.5b03340,10.1246/bcsj.20140387,10.1021/acs.joc.5b00135,10.1039/c5ob01901j,10.1039/c5ra13708j,10.1039/c5cc03113c,10.1039/c5qo00224a,10.1021/ja509077a Long 12/22/2021DEC 172014FALSEFALSEFALSEFALSE1365017645
236
249FALSEacs.orglett.7b0083110.1021/acs.orglett.7b00831https://sci-hub.wf/10.1021/acs.orglett.7b00831https://doi.org/10.1021/acs.orglett.7b00831NiC-N ActivationLongTRUE8612#N/A2017Han, JL
Ni-Catalyzed Reductive Cross-Coupling of Amides with Aryl Iodide Electrophiles via C-N Bond ActivationORG LETT
A Ni-catalyzed reductive cross-coupling reaction between two electrophiles, amides and aryl iodides, has been developed. This work is the first example using amide as an electrophile to couple with another electrophile, instead of using highly basic and pyrophoric nucleophiles. Furthermore, the Ni catalyst chemoselectively inserting the C-N bond of amide triggered the reductive cross-coupling reaction, which solves the problem that the Ni catalyst preferentially inserts the more reactive C-I bond to form a self-coupling product.
Nanjing Univ5/19/2017TRUETRUEFALSECsp2-Csp2_arE-ENX
piperidine-2,6-dione
I
Carbonyl
ArylNo baseNo BaseE-H_xxxAdded by Long10.1021/acscatal.0c00246,10.1021/jacs.7b12865,10.1021/acscatal.7b01444,10.1021/acscatal.7b03688,10.1021/acs.orglett.9b04497,10.1126/sciadv.aaw9516,10.1002/ejic.201900692,10.1021/acs.orglett.9b01164,10.1021/acs.orglett.8b01021,10.1021/acscatal.8b03436,10.1055/s-0036-1588845,10.1039/c7sc03140h10.1021/acscatal.1c05738,10.1002/anie.202114146,10.1016/j.jorganchem.2021.122042,10.1021/acs.chemrev.1c00225,10.1021/acs.joc.1c01110,10.1142/S1088424621500528,10.1021/acs.orglett.1c00464,10.1021/acssuschemeng.0c08044,10.1021/acs.orglett.0c03260,10.1021/acs.orglett.0c03342,10.1016/j.memsci.2020.118497,10.1055/s-0040-1705956,10.1021/acscatal.0c03341,10.1021/acscatal.0c03334,10.1055/s-0040-1707301,10.1016/j.trechm.2020.08.001,10.1021/acs.orglett.0c02105,10.1021/acs.orglett.0c01488,10.1002/cctc.201902290,10.1016/j.tet.2020.131201,10.1021/acs.joc.0c00227,10.1021/acs.orglett.0c00885,10.1002/adsc.202000122,10.1055/s-0039-1690055,10.1021/acs.orglett.0c00442,10.1021/acscatal.0c00246,10.1038/s41467-020-14799-8,10.1021/acs.orglett.9b04497,10.1021/acs.orglett.9b03434,10.1039/c9sc03169c,10.1002/adsc.201901188,10.1177/1747519819873514,10.1021/acs.orglett.9b02961,10.1002/chem.201903668,10.1021/acs.joc.9b02013,10.1002/slct.201902137,10.1002/ejic.201900692,10.1039/c9nj01748h,10.1126/sciadv.aaw9516,10.1021/acs.orglett.9b01164,10.1021/acs.orglett.9b01053,10.1002/ejoc.201801650,10.1002/adsc.201801577,10.1016/j.ccr.2019.01.005,10.1021/acs.orglett.8b03901,10.6023/cjoc201806038,10.1002/asia.201801317,10.3390/catal9010053,10.1021/acscatal.8b03436,10.1039/c8ob01832d,10.1039/c8cs00335a,10.1016/j.molstruc.2018.05.103,10.1021/acs.orglett.8b02911,10.1021/acs.joc.8b01922,10.1021/acscatal.8b02815,10.1002/cctc.201800511,10.1002/ejoc.201800109,10.1021/acs.orglett.8b01021,10.1021/acs.orglett.8b00949,10.1016/j.tetlet.2018.01.097,10.1021/jacs.7b12865,10.1002/slct.201800188,10.1021/acs.orglett.8b00086,10.1039/c7ob02874a,10.1021/acscatal.7b03688,10.1055/s-0036-1591853,10.1039/c7sc03140h,10.1039/c8ra01974f,10.1021/acs.orglett.7b03191,10.1039/c7ob02269g,10.1002/anie.201707102,10.1021/acscatal.7b02540,10.1021/acs.orglett.7b02288,10.1055/s-0036-1588845,10.1021/acs.orglett.7b01575,10.1021/acscatal.7b01444,10.1021/acs.orglett.7b0119911/10/2021
237
228FALSEja710944j10.1021/ja710944jhttps://sci-hub.wf/10.1021/ja710944jhttps://doi.org/10.1021/ja710944jNiC-O ActivationShihongTRUE16442282008Shi, ZJ
Ni-Catalyzed Reductive Coupling of Alkyl Acids with Unactivated Tertiary Alkyl and Glycosyl Halides
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
This work highlights Ni-catalyzed reductive coupling of alkyl acids with alkyl halides, particularly sterically hindered unactivated tertiary alkyl bromides for the production of all carbon quaternary ketones. The reductive strategy is applicable to alpha-selective synthesis of saturated, fully oxygenated C-acyl glycosides through easy manipulations of the readily available sugar bromides and alkyl acids, avoiding otherwise difficult multistep conversions. Initial mechanistic studies suggest that a radical chain mechanism (cycle B, Scheme 1) may be plausible, wherein MgCl2 promotes the reduction of Ni-II complexes.
Peking Univ3/19/2008TRUETRUETRUECsp3-ring(s)-Csp3E-NuOMgOMeMgXBenzylAlkylNo baseNo BaseStrong-0.28_xxx10.1021/acscatal.7b02817,10.1246/cl.2009.710,10.1021/ja8056503,10.1002/anie.200907287,10.1039/c7cc06106d,10.1021/ja307045r,10.1002/ejic.201900692,10.1021/acs.orglett.8b01062,10.1021/ol4011757,10.1021/jacs.7b02326,10.1039/c8sc00609a,10.1016/j.tet.2017.06.004,10.1021/ja810157e,10.1002/chem.201003731,10.1002/anie.201503936,10.1021/acscatal.6b00801,10.1021/ol502682q,10.1021/jo2000034,10.1021/ol4031815,10.1021/ja903091g,10.1021/ol203322v,10.1021/ol502583h,10.1021/ja413131m,10.1002/anie.201101191,10.1021/acs.orglett.6b02656,10.1021/ja3089422,10.1021/jacs.9b00097,10.1021/ol503707m,10.1002/chem.201103784,10.1002/chem.201603436,10.1021/ol9028308,10.1021/ol901978e,10.1021/ol901217m,10.1021/ja3013825,10.1039/c1cc11193k,10.1002/anie.200803814,10.1021/ja108547u,10.1021/om300566m,10.1002/anie.201510497,10.1021/jacs.1c03898,10.1021/ja2084509,10.1038/NCHEM.274110.6023/cjoc202106021,10.1039/d1cc05408b,10.1021/acs.inorgchem.1c01720,10.1039/c9cs00571d,10.1021/jacs.1c03898,10.1055/a-1507-4153,10.1126/science.abg5526,10.1021/acs.accounts.1c00096,10.1021/acs.accounts.1c00050,10.6023/cjoc202006077,10.1021/acs.orglett.0c04316,10.1021/acs.orglett.0c04039,10.1055/s-0040-1705986,10.1002/chem.202004132,10.6023/A20070335,10.1021/acs.orglett.0c02320,10.1021/acs.chemrev.9b00682,10.1021/jacs.0c02405,10.1021/jacs.0c00283,10.1055/s-0039-1690718,10.1039/c9cc09497k,10.1002/jccs.201900450,10.1002/adsc.201901099,10.1021/acs.orglett.9b03475,10.1016/j.tetlet.2019.150955,10.1021/acs.orglett.9b02504,10.1002/adsc.201900745,10.1021/acs.oprd.9b00235,10.1002/ejic.201900692,10.1039/c9ob00628a,10.1002/chem.201900498,10.1021/jacs.9b00097,10.1021/acs.organomet.8b00720,10.1016/j.tet.2018.10.025,10.1002/adsc.201801135,10.1039/c8cc07093h,10.1021/acs.joc.8b01763,10.1021/acsomega.8b02155,10.1021/acs.orglett.8b01696,10.1039/c8sc00742j,10.1002/adsc.201800437,10.1039/c8sc00609a,10.1021/acs.orglett.8b01062,10.1021/acscatal.8b01224,10.1002/cjoc.201700664,10.1070/RCR4795,10.1055/s-0036-1588568,10.1021/acscatal.7b02817,10.1039/c7cc06106d,10.1002/anie.201706868,10.1002/chem.201702200,10.1038/NCHEM.2741,10.1016/j.tet.2017.06.004,10.1021/acscatal.7b00772,10.1021/jacs.7b02326,10.1038/s41570-017-0025,10.1016/j.tet.2016.12.068,10.1016/j.cclet.2016.09.006,10.1021/acscatal.6b03277,10.1021/acs.orglett.6b02656,10.1002/ajoc.201600411,10.1055/s-0035-1560565,10.1021/acs.joc.6b01748,10.1002/chem.201603436,10.1021/acscatal.6b01956,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1002/anie.201510497,10.1021/acssuschemeng.5b01282,10.1016/bs.adomc.2016.07.001,10.1021/jacs.5b08621,10.1002/ejoc.201500630,10.1002/anie.201503936,10.1021/acs.accounts.5b00223,10.1186/s11671-015-0795-5,10.1021/ar500345f,10.1021/ol503707m,10.1039/c5dt03794h,10.1039/c5nj01354b,10.3998/ark.5550190.p008.915,10.1039/c4cc10084k,10.1016/j.jorganchem.2014.09.016,10.1021/ol502583h,10.1021/ol502682q,10.1055/s-0034-1378581,10.1021/jo5010636,10.1038/nature13274,10.1016/j.jorganchem.2014.01.037,10.1016/j.tet.2014.02.014,10.1515/pac-2014-5038,10.1021/ja413131m,10.1016/j.tetlet.2013.12.083,10.1002/anie.201304268,10.1039/c4dt02374a,10.1039/c4cs00206g,10.1002/ejoc.201301372,10.1021/ol4031815,10.1002/pola.26954,10.1021/ol4011757,10.1021/jp312690e,10.1021/ja312464b,10.1021/ja312087x,10.1021/ja3089422,10.1007/3418_2012_42,10.1039/c3ra42972e,10.1039/c3dt51196k,10.1039/c3ob27128e,10.1002/anie.201208843,10.1039/c3cs35521g,10.1039/c3ra44884c,10.1007/s00706-012-0838-x,10.1021/ja307045r,10.1021/om300566m,10.1055/s-0031-1291127,10.1021/ol3009842,10.1021/ja3013825,10.1021/ol203322v,10.1002/chem.201103784,10.1021/ol2033306,10.1021/ja2084509,10.1055/s-0031-1289871,10.1021/ol2023278,10.1246/cl.2011.1001,10.1002/adsc.201100285,10.1002/cctc.201100087,10.1021/ol2012007,10.1002/chem.201003731,10.1021/jo2000034,10.1021/cr100259t,10.1021/ja108547u,10.1039/c0sc00498g,10.1002/anie.201101191,10.1039/c1cc11193k,10.1021/ja106943q,10.1021/ar100082d,10.1021/ja1035557,10.1021/jo1007898,10.1055/s-0030-1258116,10.1002/ejoc.200901321,10.1021/ol9028308,10.1002/anie.200901317,10.1002/anie.200907287,10.1002/anie.201002116,10.1021/om900771v,10.1021/ol901978e,10.1021/ol901217m,10.1021/ja903091g,10.1246/cl.2009.710,10.1021/ja810157e,10.1021/om800850c,10.1002/ejoc.200801004,10.1021/ja8056503,10.1021/ja804804p,10.1016/j.tetlet.2008.04.117,10.1002/anie.200801447,10.1002/anie.200803814Kelly11/5/2021MAR 192008FALSEFALSEFALSEFALSE130113268
238
252FALSEncomms1293710.1038/ncomms12937https://sci-hub.wf/10.1038/ncomms12937https://doi.org/10.1038/ncomms12937NiC-N ActivationLongTRUE838#N/A2016
Wang, C; Uchiyama, M
Stille coupling via C-N bond cleavageNAT COMMUN
Cross-coupling is a fundamental reaction in the synthesis of functional molecules, and has been widely applied, for example, to phenols, anilines, alcohols, amines and their derivatives. Here we report the Ni-catalysed Stille cross-coupling reaction of quaternary ammonium salts via C-N bond cleavage. Aryl/alkyl-trimethylammonium salts [Ar/R-NMe3](+) react smoothly with arylstannanes in 1: 1 molar ratio in the presence of a catalytic amount of commercially available Ni(cod)(2) and imidazole ligand together with 3.0 equivalents of CsF, affording the corresponding biaryl with broad functional group compatibility. The reaction pathway, including C-N bond cleavage step, is proposed based on the experimental and computational findings, as well as isolation and single-crystal X-ray diffraction analysis of Ni-containing intermediates. This reaction should be widely applicable for transformation of amines/quaternary ammonium salts into multi-aromatics.
Univ Tokyo9/1/2016TRUETRUEFALSEyyCsp2_ar-Csp2_arE-NuNSn
NMe3+OTf-
SnMe3ArylArylNo baseNo BaseE-HNi(0)/Ni(II)_xx10.1021/acscatal.7b01058,10.1016/j.tet.2017.06.004,10.1002/ajoc.201700569,10.1021/acscatal.0c03993,10.1021/acscatal.9b00744,10.1021/jacs.9b05224,10.1021/acscatal.7b03688,10.1021/acs.orglett.9b0024210.1039/d2cc00383j,10.1039/d1ob02245h,10.1039/d1qo01240a,10.1016/j.tet.2021.132431,10.1002/aoc.6430,10.1039/d1ob01468d,10.1021/acs.joc.1c01339,10.1039/d1qo00759a,10.1021/acs.orglett.1c01503,10.6023/cjoc202009029,10.1039/d1gc00141h,10.1016/j.jorganchem.2021.121754,10.3390/molecules26051414,10.1021/acs.joc.0c02992,10.1021/acs.orglett.0c03660,10.1021/jacs.0c09616,10.1021/acscatal.0c03993,10.1021/acscatal.0c03341,10.1021/acs.joc.0c01274,10.1248/cpb.c20-00196,10.3390/molecules25153493,10.1021/acs.orglett.0c01609,10.1016/j.catcom.2020.106009,10.1039/d0qo00173b,10.1021/acs.orglett.0c00736,10.1002/chem.202000412,10.1016/j.tetlet.2020.151647,10.1039/c9ob02667c,10.1002/ajoc.201900759,10.1016/j.tetlet.2019.151454,10.1021/acs.orglett.9b04203,10.1016/j.catcom.2019.105835,10.1039/c9ob02107h,10.1016/j.tetlet.2019.151260,10.1002/adsc.201901223,10.1002/adsc.201900819,10.1021/acs.orglett.9b02820,10.1021/acscatal.9b02440,10.1021/jacs.9b05224,10.1021/acs.oprd.9b00194,10.1002/adsc.201900485,10.1016/j.isci.2019.04.038,10.1002/chem.201900886,10.1021/acscatal.9b00744,10.1021/acscatal.9b00218,10.1021/acs.orglett.9b00242,10.1021/acs.joc.8b02926,10.1021/jacs.8b08792,10.1002/slct.201803215,10.1021/acs.oprd.8b00182,10.1007/s10562-018-2446-9,10.6023/cjoc201803013,10.1002/anie.201806271,10.1039/c8cc03760d,10.1002/ajoc.201800264,10.1016/j.ijhydene.2018.02.071,10.1002/ejoc.201800223,10.1039/c8ob00488a,10.1038/s41467-018-03928-z,10.1002/anie.201712618,10.1021/acscatal.7b03688,10.1002/ajoc.201700569,10.1021/jacs.7b10537,10.1002/asia.201701342,10.1002/ijch.201700044,10.3390/met7110472,10.1016/j.jechem.2017.10.016,10.1016/j.jechem.2017.06.007,10.1021/jacs.7b08579,10.1002/cctc.201700690,10.1002/asia.201701132,10.1039/c7ce00894e,10.1016/j.tetlet.2017.07.025,10.1103/PhysRevMaterials.1.033801,10.1016/j.tet.2017.06.004,10.1021/acscatal.7b01058,10.1038/nchem.2769,10.1002/anie.20161172011/1/2021SEP2016FALSEFALSEFALSEFALSE7
239
253FALSEacs.orglett.8b0106210.1021/acs.orglett.8b01062https://sci-hub.wf/10.1021/acs.orglett.8b01062https://doi.org/10.1021/acs.orglett.8b01062NiC-N ActivationLongTRUE846272018Watson, MP
Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C-N Bond ActivationORG LETT
A nickel-catalyzed cross-coupling of benzylic pyridinium salts with arylboronic acids was developed. Coupled with chemoselective pyridinium formation, this method allows benzyl primary amines to be efficiently converted to di(hetero)-arylmethanes. Excellent heteroaryl and functional group tolerance is observed, and a one-pot procedure enables benzylic amines to be converted to diarylmethanes directly.
Univ Delaware5/18/2018TRUETRUEFALSECsp2_ar-Csp2_arE-NuNB
Triphenylpyridinium+BF4-
B(OH)2ArylArylK3PO4Ionic-PO4_xxAdded by Long10.1039/c9sc00783k,10.1055/s-0037-1610084,10.1021/jacs.9b05224,10.1021/jacs.9b00111,10.1021/acs.orglett.9b01014,10.1021/acs.orglett.9b0449710.1055/s-0040-1719881,10.1039/d1gc04184c,10.1021/acs.orglett.1c03870,10.1021/jacs.1c10932,10.1021/acs.joc.1c02162,10.1002/adsc.202100940,10.3390/molecules26195947,10.1021/acs.orglett.1c02708,10.1002/ajoc.202100438,10.1021/acs.joc.1c01555,10.1021/acs.inorgchem.1c01427,10.1039/d1cc03292e,10.1021/acs.orglett.1c01959,10.1021/acs.orglett.1c01758,10.1039/c9cs00571d,10.1021/acscatal.1c01860,10.1002/cctc.202100672,10.1021/acs.orglett.1c01716,10.1039/d1sc01217g,10.1021/acscatal.1c01416,10.1016/j.tetlet.2021.153071,10.1039/d1sc00986a,10.1039/d1cc00039j,10.1021/acs.orglett.1c00178,10.1021/acs.orglett.1c00346,10.1021/acs.orglett.0c04287,10.1039/d0cc07632e,10.1002/ejoc.202001193,10.1039/d0ob01807d,10.1002/ajoc.202000480,10.1021/acs.orglett.0c03347,10.1021/acscatal.0c03341,10.1039/d0cc05633b,10.1021/jacs.0c08595,10.1021/acs.orglett.0c01831,10.1021/acs.orglett.0c01592,10.1002/anie.202006048,10.1002/adsc.202000457,10.1021/acs.oprd.0c00104,10.1021/acs.orglett.0c01284,10.1002/anie.201914555,10.3762/bjoc.16.74,10.1021/acs.orglett.0c00554,10.1002/anie.201911660,10.1039/d0sc00225a,10.1002/chem.202000412,10.1021/acs.orglett.9b04497,10.1055/s-0039-1690703,10.1039/c9ob02107h,10.1039/c9qo01175g,10.1021/acs.orglett.9b03899,10.1021/acs.orglett.9b03284,10.1039/c9sc03765a,10.3390/molecules24193523,10.1021/acscatal.9b03084,10.1039/c9cc05385a,10.1021/acs.orglett.9b02643,10.6023/A19040121,10.1002/adsc.201900576,10.1021/acs.orglett.9b02534,10.1021/jacs.9b05224,10.1002/chem.201901397,10.1021/acs.orglett.9b01669,10.1038/s41929-019-0292-9,10.1039/c9sc00783k,10.1021/acs.orglett.9b01014,10.1002/anie.201814452,10.1002/chem.201900886,10.1021/acscatal.9b00218,10.1002/anie.201813689,10.1039/c8ob02786b,10.1021/jacs.9b00111,10.2174/1570193X16666181228102304,10.1021/acscatal.8b04191,10.1039/c8qo01046c,10.1021/acscatal.8b03437,10.1002/chem.201804246,10.1002/anie.201809608,10.1039/c8cc07093h,10.1021/jacs.8b07103,10.1002/anie.201806271,10.1055/s-0037-161008411/10/2021
240
249FALSEja805650310.1021/ja8056503https://sci-hub.wf/10.1021/ja8056503https://doi.org/10.1021/ja8056503NiC-O ActivationShihongTRUE32478282008Shi, ZJ
Direct benzylic alkylation via Ni-catalyzed selective benzylic sp(3) C-O activation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
This article demonstrates the first cross coupling of benzyl ether with Grignard reagents via Ni-catalyzed benzylic sp(3) C-O activation with high efficiency and excellent chemoselectivity. Benzylic sp(3) C-O and aryl sp(2) C-O were differentiated, controlled by ligands.
Peking Univ11/5/2008TRUETRUEFALSECsp2_ar-Csp2_arE-NuOBOPivB(OH)2ArylArylK3PO4Ionic-PO4Medium0.33TMxxx10.1039/c0cc03107k,10.1021/om300566m,10.1021/acs.orglett.7b00556,10.1021/ol9001587,10.1002/chem.201003731,10.1021/ol203322v,10.1021/ol101592r,10.1021/jo3001194,10.1021/jo4005537,10.1002/ejoc.200900067,10.1002/adsc.201400460,10.1038/s41929-020-00560-3,10.1021/jo2022982,10.1021/ol901217m,10.1039/c8sc00609a,10.1039/c1cc11193k,10.1002/ejoc.201200444,10.1002/chem.201103050,10.1002/chem.200902785,10.1021/ol503061c,10.1021/ja907700e,10.1021/ja810157e,10.1016/j.tet.2012.04.005,10.1021/acs.joc.6b01627,10.1002/anie.201101461,10.1002/chem.201003403,10.1021/ol9028308,10.1002/adsc.201000710,10.1021/ja200398c,10.1021/jo300547v,10.1002/anie.201806790,10.1021/jacs.6b11412,10.1021/jo1024464,10.1021/acs.orglett.6b02265,10.1039/c7cc06717h,10.1021/acscatal.5b01021,10.1021/ja903091g,10.1021/ol4011757,10.1021/acscatal.0c03993,10.1021/acscatal.9b00744,10.1246/cl.2011.913,10.1038/NCHEM.2388,10.1002/anie.201511486,10.1002/ejoc.201000147,10.1002/chem.201000420,10.1021/ja906477r,10.1002/adsc.201100151,10.1038/s41467-020-20725-9,10.1002/anie.200900329,10.1002/chem.201103784,10.1002/anie.200907287,10.1021/acscatal.8b03436,10.1021/ja210249h,10.1039/c1sc00230a,10.1021/ol9029534,10.1021/om500452c,10.1021/jacs.0c06995,10.1021/jo202037x,10.1002/anie.201007325,10.1021/ol901978e,10.1039/c5sc02942b,10.1021/ol401727y,10.1055/s-0036-1588845,10.1002/anie.201412051,10.1039/c3cc46663a,10.1039/c4qo00321g,10.1002/anie.200803814,10.1021/acscatal.6b00801,10.1021/jo2000034,10.1021/acscatal.7b01058,10.1021/acs.orglett.9b00242,10.1002/ejoc.201001519,10.1021/acscatal.7b00941,10.1021/jacs.7b04973,10.1021/jacs.1c09797,10.1021/acs.orglett.6b01398,10.1021/cs501045v,10.1002/anie.20090735910.1021/acs.orglett.2c00267,10.1039/d1ob02051j,10.1021/acsomega.1c05770,10.1021/acs.orglett.1c04123,10.1021/acsomega.1c05770,10.1021/jacs.1c10042,10.1021/jacs.1c09797,10.1021/acs.orglett.1c03048,10.1002/ejoc.202100955,10.1039/d1ob01619a,10.1002/aoc.6430,10.1021/acscatal.1c02952,10.6023/cjoc202103040,10.1039/d1cc04038c,10.1039/d1ob00955a,10.1002/cjoc.202100276,10.1002/aoc.6378,10.1039/c9cs00571d,10.1002/anie.202103465,10.1021/acs.organomet.1c00085,10.1055/a-1507-6419,10.1055/a-1503-6330,10.6023/cjoc202100028,10.1039/d0cc08389e,10.1038/s41929-020-00560-3,10.1002/chem.202004437,10.1038/s41467-020-20725-9,10.1055/a-1349-3543,10.1080/14756366.2021.1900165,10.1039/d0dt01119c,10.1021/acs.orglett.0c03342,10.1038/s41467-020-19944-x,10.1021/acscatal.0c03993,10.1002/cctc.202001347,10.1055/a-1306-3228,10.1002/cjoc.202000319,10.1021/acscatal.0c03334,10.1021/acs.chemrev.0c00088,10.1021/jacs.0c06995,10.1039/d0ra02272a,10.1021/acscatal.0c01462,10.1002/anie.202006586,10.1021/jacs.0c05730,10.1039/d0sc01641a,10.1039/d0sc01585g,10.1021/acs.organomet.0c00338,10.1002/cjoc.201900506,10.1021/acscatal.9b05049,10.1039/c9qo01095e,10.1134/S1070363219120405,10.1021/jacs.9b08586,10.1021/acscatal.9b02636,10.1016/j.isci.2019.08.021,10.1021/acs.orglett.9b02050,10.1038/s42004-019-0182-8,10.1039/c9dt00455f,10.1039/c9ra02394a,10.1002/adsc.201801586,10.1039/c9ob00313d,10.1021/acscatal.9b00744,10.6023/cjoc201809027,10.1002/asia.201801862,10.1055/s-0037-1611720,10.1021/acs.orglett.9b00242,10.1016/j.apsusc.2018.09.154,10.1021/acs.organomet.8b00720,10.1002/slct.201803105,10.1007/3418_2018_19,10.1021/acs.accounts.8b00408,10.1021/acscatal.8b03436,10.1016/j.tet.2018.10.025,10.1021/acs.organomet.8b00199,10.1021/acsomega.8b02155,10.1002/adsc.201800729,10.1002/anie.201805486,10.1002/anie.201806790,10.1021/acs.orglett.8b01646,10.1016/j.jorganchem.2018.01.019,10.1039/c8sc00609a,10.1021/acscatal.8b01224,10.1002/aoc.4273,10.1055/s-0036-1591523,10.1002/cjoc.201700664,10.1021/acs.orglett.7b03713,10.1021/acs.orglett.8b00080,10.1039/c7cc08709h,10.1021/acs.orglett.7b03669,10.1021/acs.joc.7b02588,10.1039/c7cc06717h,10.1055/s-0036-1588568,10.1039/c7nj02488f,10.1055/s-0036-1588508,10.1021/jacs.7b04973,10.1021/acs.joc.7b01566,10.1021/acsomega.7b01165,10.1055/s-0036-1588845,10.1021/jacs.7b03159,10.1002/asia.201700313,10.1021/acscatal.7b00941,10.1039/c7qo00068e,10.1021/acscatal.7b01058,10.1021/acs.orglett.7b00556,10.1021/acscatal.6b02912,10.1002/anie.201611720,10.1021/acscatal.6b03344,10.1021/acscatal.7b00245,10.1038/s41570-017-0025,10.1021/jacs.6b12329,10.1021/jacs.6b11412,10.1021/acscatal.6b02964,10.1039/c7ra02549a,10.1021/acs.joc.6b02093,10.1016/j.jorganchem.2016.09.026,10.1002/chem.201604160,10.1021/acs.joc.6b01627,10.1021/acscatal.6b01956,10.1021/acs.orglett.6b02265,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1021/acs.orglett.6b01398,10.1016/j.tet.2016.03.074,10.1002/anie.201601914,10.1016/j.tet.2016.02.069,10.1002/chem.201504959,10.1002/anie.201511486,10.1002/chem.201503090,10.1016/bs.adomc.2016.07.001,10.1039/c5ra27859g,10.1039/c5cc10005d,10.1039/c5ee03256c,10.1038/NCHEM.2388,10.1016/j.tetlet.2015.10.009,10.1002/anie.201505699,10.1002/chem.201502338,10.1002/adsc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Long 11/5/2021NOV 52008FALSEFALSEFALSEFALSE1304414468
241
248FALSEja806244b10.1021/ja806244bhttps://sci-hub.wf/10.1021/ja806244bhttps://doi.org/10.1021/ja806244bNiC-O ActivationGerryTRUE32280542008Garg, NK
Biaryl Construction via Ni-Catalyzed C-O Activation of Phenolic Carboxylates
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Biaryl scaffolds were constructed via Ni-catalyzed aryl C-O activation by avoiding cleavage of the more reactive acyl C-O bond aryl carboxylates. Now aryl esters, in general, can be successfully employed in cross-coupling reactions for the first time. The substrate scope and synthetic utility of the chemistry were demonstrated by the syntheses of more than 40 biaryls and by constructing complex organic molecules. Water was observed to play an important role in facilitating this transformation.
Univ Calif Los Angeles
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Cross-Coupling Reactions of Aryl Pivalates with Boronic Acids
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
The first cross-coupling of acylated phenol derivatives has been achieved. In the presence of an air-stable Ni(II) complex, readily accessible aryl pivalates participate in the Suzuki-Miyaura coupling with arylboronic acids. The process is tolerant of considerable variation in each of the cross-coupling components. In addition, a one-pot acylation/cross-coupling sequence has been developed. The potential to utilize an aryl pivalate as a directing group has also been demonstrated, along with the ability to sequentially cross-couple an aryl bromide followed by an aryl pivalate, using palladium and nickel catalysis, respectively.
Tsinghua Univ7/1/2009TRUETRUETRUECsp2_ar-Csp2_arE-NuOBOAcB(OH)2ArylArylK3PO4Ionic-PO4Medium0.31_10.1002/anie.200907287,10.1021/acs.joc.5b00669,10.1021/jacs.9b00097,10.1021/jacs.1c08399,10.1021/ol4011757,10.1039/c8sc00609a,10.1021/jacs.7b04279,10.1021/acscatal.7b00941,10.1002/anie.202004116,10.1055/s-0036-1590863,10.1021/jo2022982,10.1002/adsc.201100151,10.1021/ja200398c,10.1021/ol9029534,10.1021/jacs.0c04670,10.1002/anie.201101461,10.1021/jacs.7b12865,10.1002/chem.201103784,10.1021/jacs.7b04973,10.1002/chem.200902785,10.1002/adsc.201400460,10.1039/c7qo00850c,10.1021/ja907700e,10.1038/s41929-020-00560-3,10.1039/c1sc00230a,10.1021/acscatal.5b01021,10.1002/anie.201510497,10.1021/ol203322v,10.1021/ol101592r,10.1021/acs.orglett.6b01398,10.1021/jo2000034,10.1246/cl.2011.913,10.1002/anie.201511486,10.1021/jo400553710.1021/acscatal.1c04895,10.1021/jacs.1c08399,10.1002/anie.202110785,10.1039/d1cc05408b,10.1039/d1dt02551a,10.1021/acs.organomet.1c00370,10.6023/cjoc202103040,10.1039/d1ob00955a,10.1021/acs.accounts.1c00050,10.1016/j.cclet.2020.04.005,10.1038/s41929-020-00560-3,10.1002/chem.202004437,10.1016/j.mcat.2020.111344,10.1055/s-0040-1706662,10.1055/a-1349-3543,10.1002/cctc.202001462,10.1055/a-1306-3228,10.1021/acscatal.0c03341,10.1021/acs.chemrev.0c00088,10.1002/anie.202004116,10.1021/jacs.0c04670,10.1002/adsc.202000186,10.1002/cjoc.201900506,10.1002/ajoc.202000110,10.1021/acscatal.9b03827,10.1021/acscatal.9b02636,10.1039/c9nj01061k,10.1039/c9dt00455f,10.1021/acs.organomet.8b00878,10.1021/jacs.9b00097,10.1021/acs.organomet.8b00883,10.1002/chem.201805987,10.1021/acs.chemrev.8b00361,10.1021/acs.organomet.8b00720,10.1007/3418_2018_19,10.1016/j.tet.2018.10.025,10.3390/molecules23112859,10.1002/cctc.201800898,10.3390/molecules23102681,10.1021/jacs.8b04479,10.1021/acs.orglett.8b01646,10.1016/j.jorganchem.2018.01.019,10.1039/c8sc00609a,10.7503/cjcu20170652,10.1021/jacs.7b12865,10.1021/acs.joc.7b03107,10.1021/acscatal.7b04105,10.1002/ajoc.201700645,10.1039/c7qo00850c,10.1039/c7qo00934h,10.1021/acs.orglett.7b03713,10.1021/acs.orglett.7b03753,10.1021/acs.orglett.7b03669,10.1039/c7cc08416a,10.1002/chem.201703266,10.1055/s-0036-1590863,10.1021/jacs.7b09482,10.1007/s11426-017-9025-1,10.1039/c7dt02532g,10.1021/acs.organomet.7b00632,10.1021/jacs.7b04973,10.1021/acs.joc.7b01637,10.1248/cpb.c17-00487,10.1021/acs.orglett.7b02012,10.1021/jacs.7b04279,10.1002/asia.201700313,10.1021/acscatal.7b00941,10.1039/c7qo00068e,10.1021/acs.organomet.7b00095,10.1021/acs.organomet.7b00208,10.1021/acscatal.6b02912,10.1021/acscatal.7b00245,10.1002/chem.201604893,10.1021/jacs.6b12329,10.1021/acs.joc.6b02642,10.1002/ejic.201601351,10.1021/acs.joc.6b02093,10.1139/cjc-2016-0287,10.1002/chem.201604160,10.1021/acscatal.6b01956,10.1007/s41061-016-0043-1,10.1021/acs.orglett.6b01398,10.1002/anie.201510497,10.1021/acs.inorgchem.5b02664,10.1021/jacs.6b01877,10.1021/acs.joc.5b02667,10.1021/acscatal.5b02058,10.1002/anie.201511486,10.1016/bs.adomc.2016.07.001,10.1039/c6ob00607h,10.1039/c5ra27859g,10.1021/acscatal.5b02089,10.1016/j.ccr.2015.02.004,10.1007/s11426-016-0330-3,10.1002/chem.201406680,10.1021/acs.organomet.5b00710,10.1002/asia.201500599,10.1002/chem.201502114,10.1021/acs.chemrev.5b00163,10.1002/ejoc.201500630,10.1021/acscatal.5b01021,10.1007/s11426-015-5360-7,10.1021/acs.joc.5b00669,10.1007/s11144-015-0839-y,10.1021/acs.jpca.5b00569,10.1021/ar500345f,10.1021/ol503560e,10.1039/c5nj01354b,10.1007/978-3-319-13054-5_7,10.1039/c5ra01363a,10.1016/j.cclet.2014.10.021,10.1016/S1872-2067(14)60217-5,10.1016/j.tetlet.2014.11.020,10.1021/jo501814n,10.1016/j.catcom.2014.08.010,10.1063/1674-0068/27/06/640-646,10.1002/asia.201402746,10.1021/om500921d,10.1016/j.jaap.2014.08.002,10.1016/j.jorganchem.2014.08.015,10.1021/ja50711741,10.1002/adsc.201400460,10.1021/jo501321m,10.1016/j.ccr.2014.02.023,10.1021/ja4127455,10.1021/om5001327,10.1016/j.jorganchem.2013.12.047,10.3866/PKU.WHXB201403241,10.1002/chem.201303249,10.1021/om401141r,10.1002/cjoc.201400015,10.1016/j.inoche.2013.12.026,10.1021/ja4118413,10.1021/jo4023974,10.1021/jo402392t,10.1039/c4ra07455f,10.1039/c4dt02374a,10.1080/00268976.2014.886738,10.6023/cjoc201307035,10.1016/j.comptc.2013.10.019,10.1016/j.comptc.2013.11.012,10.1039/c3ob42088d,10.1021/ja409803x,10.1002/asia.201300688,10.6023/A13040455,10.1021/ja4076716,10.1002/chem.201203666,10.1021/om400370v,10.1016/j.comptc.2013.04.015,10.1021/ol4011757,10.1002/aoc.3000,10.1021/jo4005537,10.1002/adsc.201300091,10.1007/s11426-012-4795-3,10.1021/ja312464b,10.1002/aoc.2970,10.1021/ja311940s,10.1002/cjoc.201200753,10.1021/jp3045498,10.1007/3418_2012_42,10.1039/c3cc45836a,10.1039/c3ra42434k,10.1039/c3sc22242j,10.1039/c3dt31898b,10.1039/c3cs35521g,10.1021/op300236f,10.1002/chem.201202623,10.1002/chem.201201425,10.1021/ma301797w,10.1002/adsc.201200364,10.1007/s11426-012-4711-x,10.1016/j.comptc.2012.08.010,10.1021/om300329z,10.1016/j.comptc.2012.02.014,10.1002/chem.201103882,10.1021/ja300326t,10.1021/ol203322v,10.1002/chem.201103784,10.1021/jo2022982,10.1039/c2ob25581b,10.1039/c1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Mechanism of Ni-Catalyzed Selective C-O Bond Activation in Cross-Coupling of Aryl Esters
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Ni-catalyzed selective C-O bond activation opens a door for the cross-coupling of aryl esters. The present study reports a thorough theoretical analysis of Ni-catalyzed cross-coupling between aryl esters and arylboronic acids, with an emphasis on explaining the cause for the surprising selectivity in C-O activation. The overall catalytic cycle is found to include three basic steps: oxidative addition, transmetalation, and reductive elimination. Oxidative addition of Ar-OAc to Ni(0) in the presence of PCy3 ligand proceeds through the monophosphine pathway (instead of the alternative two-phosphine pathway) with a relatively low barrier of +22.9 kcal/mol. Transmetalation proceeds via a base-assisted mechanism with a barrier of +31.2 kcal/mol. Reductive elimination is the most facile step in the whole catalytic cycle. Comparatively, oxidative addition of ArO-Ac to Ni(0) is a more facile process (barrier = +14.2 kcal/mol) than oxidative addition of Ar-OAc to Ni(0). However, the former process is associated with a fairly low reverse barrier, and its product does not transmetalate easily (barrier = +33.1 kcal/mol). By comparison, the latter process is an irreversible reaction, and its product transmetalates more readily. These results explain why only the cross-coupling products from the Ar-OAc activation (but not from the ArO-Ac activation) were observed in experiments.
Univ Tokyo7/15/2009TRUETRUEFALSECsp2_ar-Csp2_arE-NuOMgOTfMgXArylArylNo baseNo 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152009FALSEFALSEFALSEFALSE131279590
244
243FALSEja906477r10.1021/ja906477rhttps://sci-hub.wf/10.1021/ja906477rhttps://doi.org/10.1021/ja906477rNiC-O ActivationLongTRUE26057542009Garg, NK
Hydroxyphosphine Ligand for Nickel-Catalyzed Cross-Coupling through Nickel/Magnesium Bimetallic Cooperation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
We report here that hydroxyphosphine ligands (PO ligands) significantly accelerate nickel-catalyzed cross-coupling reactions of unreactive aryl electrophiles and Grignard reagents. The new catalytic system based on the nickel-PO-Grignard combination allows facile activation of unreactive aryl halides such as fluorides, chlorides, polyfluorides, and polychlorides as well as phenol derivatives such as carbamates and phosphates to give the corresponding cross-coupling products in good to excellent yields. We ascribe the high catalytic activity to a nickel phosphine/magnesium alkoxide bimetallic species that forms from the nickel precatalyst, the PO ligand, and the Grignard reagent and undergoes activation of the aryl-X bond by a cooperative push-pull action of the nucleophilic nickel and Lewis acidic magnesium centers. This mechanistic conjecture was corroborated by kinetic, isotope effect experiments and density functional theory calculations. Being distinct from the conventional three-centered mechanism for oxidative addition, the proposed mechanism for the C-X bond activation offers a new concept for the design of cross-coupling reactions as well as other homogeneous catalyses involving activation of electrophilic substrates.
Univ Calif Los Angeles
12/16/2009TRUETRUEFALSECsp2_ar-Csp2_arE-NuOBOBocB(OH)2ArylArylK3PO4Ionic-PO4Medium0.31TM10.1002/ejoc.201200444,10.1016/j.tet.2012.04.005,10.1002/chem.201003403,10.1021/ol302112q,10.1002/chem.201103050,10.1021/cs501045v,10.1021/ol101592r,10.1002/anie.201412051,10.1021/acs.orglett.6b01398,10.1021/acscatal.5b01021,10.1038/s41467-020-20725-9,10.1002/anie.201806790,10.1021/ol301847m,10.1021/jo2022982,10.1021/jacs.1c09797,10.1021/ol200267b,10.1021/jo202037x,10.1021/ol9029534,10.1021/acs.orglett.7b00556,10.1039/c4qo00321g,10.1021/acscatal.8b03436,10.1039/c0cc03107k,10.1021/ol4011757,10.1039/c1sc00230a,10.1002/anie.200907359,10.1021/acscatal.7b00941,10.1021/jo501291y,10.1021/jacs.9b05461,10.1021/om500452c,10.1021/om300566m,10.1002/anie.201007325,10.1021/jo300547v,10.1021/acscatal.9b00744,10.1246/cl.2011.913,10.1002/adsc.201000710,10.1021/jo1024464,10.1002/anie.200907287,10.1021/ja210249h,10.1016/j.tet.2013.04.096,10.1021/jacs.6b11412,10.1021/acscatal.5b00498,10.1021/ol203322v,10.1021/jacs.7b04973,10.1021/acs.joc.6b01627,10.1002/ejoc.201000147,10.1021/acscatal.7b02014,10.1021/jo4005537,10.1002/ejoc.201001519,10.1002/chem.201000420,10.1002/anie.201101461,10.1039/c1cc11193k,10.1021/jo3001194,10.1021/ja200398c,10.1021/acscatal.6b00801,10.1021/ol401727y,10.1021/jo2000034,10.1002/chem.20100373110.1039/d1sc06701j,10.1021/acs.orglett.2c00267,10.1021/acs.inorgchem.1c02127,10.1021/jacs.1c09797,10.1021/acs.orglett.1c01879,10.1021/acs.organomet.1c00369,10.1007/s11164-021-04528-1,10.1055/a-1548-8362,10.1039/c9cs00571d,10.1021/acscatal.0c05481,10.1038/s41467-020-20725-9,10.1055/a-1349-3543,10.1002/adsc.202001262,10.1002/chem.202004132,10.1002/cctc.202001347,10.1021/acscatal.0c03334,10.1021/acs.joc.0c01732,10.1021/acs.chemrev.0c00088,10.1039/d0nj01610a,10.1016/j.mcat.2020.110915,10.1016/j.tet.2020.131216,10.1002/aoc.5662,10.1021/acs.orglett.0c01123,10.1002/cjoc.201900506,10.1021/acsomega.9b04450,10.1007/s11426-019-9679-6,10.1021/acsomega.9b03989,10.1021/acs.orglett.9b04119,10.1021/jacs.9b08586,10.1021/acscatal.9b02636,10.1021/acs.organomet.9b00543,10.1021/acs.joc.9b01103,10.1021/acs.orglett.9b02621,10.1016/j.jcat.2019.07.026,10.1039/c9nj02810b,10.1021/jacs.9b05461,10.1039/c9dt00455f,10.1002/adsc.201801586,10.1039/c9ob00313d,10.1039/c8tc06517a,10.1021/acscatal.9b00744,10.1016/j.tet.2019.01.015,10.1002/chem.201802635,10.1039/c8nj05503c,10.1021/acs.organomet.8b00720,10.1021/acs.organomet.8b00307,10.1007/3418_2018_19,10.1021/acscatal.8b03436,10.1016/j.tet.2018.10.025,10.1021/acs.organomet.8b00589,10.1038/s41557-018-0110-z,10.1002/anie.201804794,10.1002/anie.201806790,10.1021/acs.joc.8b01176,10.1021/acscatal.8b00933,10.1016/j.jorganchem.2018.01.019,10.1021/acs.joc.7b03210,10.1021/acscatal.8b00230,10.1038/s41557-018-0021-z,10.1055/s-0036-1591523,10.1021/acs.orglett.7b03713,10.1039/c7cc08709h,10.1055/s-0036-1591853,10.1002/ejoc.201701142,10.1021/acs.chemrev.7b00588,10.1039/c7cc07777g,10.1055/s-0036-1590985,10.1021/acs.orglett.7b03059,10.1055/s-0036-1588508,10.1021/acs.organomet.7b00642,10.1021/jacs.7b04973,10.1016/j.jorganchem.2017.02.004,10.1021/acscatal.7b02014,10.1021/acscatal.7b00941,10.1002/ejoc.201700660,10.1039/c6gc03465a,10.1021/acs.orglett.7b00556,10.1021/acscatal.6b02912,10.1002/adsc.201601105,10.1038/s41570-017-0025,10.1021/jacs.6b13346,10.1021/acscatal.6b03277,10.1021/jacs.6b11412,10.1021/acscatal.6b02964,10.1039/c7ra02549a,10.1016/j.jorganchem.2016.09.026,10.1021/acs.orglett.6b02330,10.1016/j.jorganchem.2016.08.017,10.1021/acs.joc.6b01627,10.1021/acscatal.6b01956,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1021/acs.orglett.6b01398,10.1002/anie.201601914,10.1016/j.tet.2016.02.069,10.1021/acs.joc.5b02667,10.1016/j.tet.2015.12.028,10.1002/ejoc.201501492,10.1016/bs.adomc.2016.07.001,10.1039/c5ra27859g,10.1039/c5nj01833a,10.1002/anie.201505699,10.1002/chem.201502689,10.1002/ejoc.201500987,10.1002/adsc.201500515,10.1002/ejoc.201500630,10.1021/acscatal.5b01021,10.1002/adsc.201500304,10.1021/acs.orglett.5b01466,10.1016/j.tet.2015.02.088,10.1002/adsc.201400850,10.1021/acscatal.5b00498,10.1002/cctc.201500079,10.1016/j.jorganchem.2015.01.009,10.1002/anie.201412051,10.1246/cl.141084,10.1021/ed500158p,10.1021/ar500345f,10.1021/ja512498u,10.1021/ol503560e,10.1016/j.catcom.2014.08.037,10.1039/c4qo00321g,10.1039/c4qo00331d,10.1039/C5QO00243E,10.1039/c5ob00431d,10.1021/ja5099935,10.1021/om500452c,10.1021/ol5024344,10.1002/ejoc.201402919,10.1021/cs501045v,10.1007/s11426-014-5138-3,10.1021/jo501291y,10.1055/s-0033-1339108,10.1021/jo500507s,10.1002/ejoc.201402120,10.1021/ol500707w,10.1021/ol500258q,10.1515/pac-2014-5038,10.1021/cr400230c,10.1021/ol500310u,10.1021/ja4118413,10.1021/cs4009946,10.1021/ja410883p,10.6023/cjoc201307035,10.1039/c3ob41382a,10.1021/ja409803x,10.1002/ejoc.201300592,10.1002/jhet.1090,10.1002/asia.201300688,10.1595/147106713X672311,10.1021/ol401727y,10.1016/j.tet.2013.04.096,10.1021/ol4011757,10.1021/jo4005537,10.1021/ol401021x,10.1002/ejoc.201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245
235FALSEja907700e10.1021/ja907700ehttps://sci-hub.wf/10.1021/ja907700ehttps://doi.org/10.1021/ja907700eNiC-O ActivationLongTRUE19948622009Snieckus, V
Suzuki-Miyaura Coupling of Aryl Carbamates, Carbonates, and Sulfamates
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Queens Univ12/16/2009TRUEFALSEFALSECsp2_ar-Csp2_arE-NuOB
OCONEt2
B(OH)2HetArylK3PO4Ionic-PO4Medium0.31TMLong added10.1021/ja200398c,10.1021/acscatal.7b01058,10.1002/ejoc.201001519,10.1021/ja210249h,10.1021/acscatal.8b03436,10.1021/ol9029534,10.1016/j.tet.2012.04.005,10.1002/anie.201101461,10.1021/jo1024464,10.1021/acscatal.5b01021,10.1021/jacs.1c09797,10.1021/jo2022982,10.1021/jo3001194,10.1002/anie.201806790,10.1002/anie.200907359,10.1002/ejoc.201200444,10.1021/ja2084509,10.1021/jo2000034,10.1002/chem.201000420,10.1002/chem.201003731,10.1039/c0cc03107k,10.1246/cl.2011.913,10.1038/NCHEM.2388,10.1002/anie.201007325,10.1002/chem.201103784,10.1039/c4qo00321g,10.1021/ol101592r,10.1021/ol203322v,10.1002/chem.201003403,10.1021/cs501045v,10.1021/ol302112q,10.1021/acs.orglett.6b00819,10.1021/ol4011757,10.1021/jo4005537,10.1039/c1sc00230a,10.1021/jacs.6b11412,10.1021/acs.orglett.5b00241,10.1021/om500452c,10.1002/ejoc.201000147,10.1021/ol401727y,10.1021/ol503061c,10.1039/c1cc11193k,10.1021/jo300547v,10.1021/jacs.7b04973,10.1021/acs.orglett.6b01398,10.1021/acs.joc.6b01627,10.1021/om300566m,10.1002/adsc.20100071010.1021/acs.joc.1c02580,10.1021/jacs.1c09797,10.1021/acs.orglett.1c03048,10.1002/cjoc.202100276,10.1039/c9cs00571d,10.1055/a-1349-3543,10.1021/acs.joc.0c01732,10.1021/acs.chemrev.0c00088,10.1016/j.inoche.2020.107993,10.1021/acs.orglett.0c01937,10.1039/d0sc01585g,10.1021/acs.orglett.0c01123,10.1002/cjoc.201900506,10.1021/acsomega.9b04450,10.1021/acs.orglett.0c00633,10.1039/c9cc08663c,10.1021/acs.joc.9b01103,10.1016/j.jcat.2019.07.026,10.1055/s-0037-1609636,10.1039/c8nj05503c,10.1021/acs.organomet.8b00720,10.1007/3418_2018_19,10.1021/acscatal.8b03436,10.1016/j.tet.2018.10.025,10.1055/s-0037-1610273,10.1055/s-0037-1611053,10.1002/anie.201806790,10.1021/acscatal.8b00933,10.1016/j.jorganchem.2018.01.019,10.1021/acs.orglett.8b00755,10.1021/acscatal.8b01224,10.1021/acs.joc.7b03210,10.1021/acscatal.8b00230,10.1002/ejoc.201701142,10.1021/acs.chemrev.7b00588,10.1039/c7cc07777g,10.1055/s-0036-1590985,10.1021/jacs.7b04973,10.1055/s-0036-1590819,10.1021/acs.joc.7b00550,10.1002/ejoc.201700660,10.1021/acscatal.7b01058,10.1021/acs.organomet.7b00208,10.1016/j.tet.2017.02.021,10.1021/acscatal.6b02912,10.1038/s41570-017-0025,10.1021/jacs.6b11412,10.1021/acscatal.6b02964,10.1021/acs.joc.6b02093,10.1002/ejoc.201600933,10.1021/acs.joc.6b01627,10.1055/s-0035-1562343,10.1002/chem.201601584,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1002/cctc.201600234,10.1021/acs.orglett.6b01398,10.1002/anie.201601914,10.1021/acs.orglett.6b00819,10.1016/bs.adomc.2016.07.001,10.1038/NCHEM.2388,10.1002/anie.201505699,10.1002/chem.201502689,10.1021/acs.orglett.5b01913,10.1002/adsc.201500515,10.1002/ejoc.201500630,10.1021/acscatal.5b01021,10.1021/acs.orglett.5b01229,10.1002/adsc.201500304,10.1016/j.tet.2015.02.088,10.1038/ncomms8508,10.1021/acs.orglett.5b00241,10.1246/cl.141084,10.1021/ar500345f,10.1039/c4qo00321g,10.1039/c4qo00331d,10.1039/C5QO00243E,10.1039/c5cc02094h,10.1021/ol503061c,10.1021/om500452c,10.1021/ol5024344,10.1002/ejoc.201402919,10.1021/cs501045v,10.1021/ja503819x,10.1007/s11426-014-5138-3,10.1055/s-0033-1339108,10.1021/ol501180q,10.1038/nature13274,10.1021/ol500707w,10.1021/ol500258q,10.1515/pac-2014-5038,10.1021/ol500310u,10.1021/ja4118413,10.1021/cs4009946,10.1021/ja410883p,10.3184/174751914X13857348538466,10.6023/cjoc201307035,10.1021/ja409803x,10.1002/jhet.1090,10.1002/asia.201300688,10.1595/147106713X672311,10.1021/ol401727y,10.1021/ol4011757,10.1021/jo4005537,10.1021/ol303130j,10.1007/3418_2012_42,10.1039/c3sc22242j,10.1002/cctc.201200417,10.1039/c3sc00052d,10.1039/c3cs35521g,10.1002/ejoc.201200914,10.1021/op300236f,10.1021/op200238p,10.1002/ejoc.201200918,10.1002/adsc.201200364,10.1021/om300566m,10.1021/ol302112q,10.1021/jo300547v,10.1021/ol301681z,10.1002/ejoc.201200444,10.1002/ejoc.201200368,10.1016/j.tet.2012.04.005,10.1021/ol300908g,10.1021/ol301275u,10.1021/ol300671y,10.1021/ja300326t,10.1021/om300154m,10.1021/jo3001194,10.1021/om201271y,10.1021/ol203322v,10.1002/chem.201103784,10.1021/jo2022982,10.1021/ja210249h,10.1021/ja2084509,10.1002/anie.201202466,10.1002/ejoc.201101527,10.1002/anie.201207428,10.1039/c2ob25395j,10.1039/c1cc15845g,10.1021/ja207759e,10.1246/cl.2011.1254,10.1021/ol2020847,10.1246/cl.2011.913,10.1246/cl.2011.1001,10.1246/cl.2011.907,10.1021/ol201469r,10.1002/adsc.201100101,10.1021/ol200764g,10.1002/adsc.201000975,10.1021/ja200398c,10.1002/chem.201003731,10.1021/jo2000034,10.1021/jo1024464,10.1002/chem.201003403,10.1002/ejoc.201001519,10.1021/cr100259t,10.1021/cr1002276,10.1002/adsc.201000710,10.1039/c0sc00498g,10.1002/anie.201007464,10.1002/anie.201007325,10.1002/anie.201101461,10.1002/anie.201103599,10.1039/c1cc11193k,10.1039/c1sc00230a,10.1002/chem.201001943,10.1002/chem.201002273,10.1021/ar100082d,10.4155/FMC.10.266,10.1246/cl.2010.1050,10.1021/ol101493m,10.1021/ol101592r,10.1002/adsc.201000267,10.3762/bjoc.6.70,10.1021/ol100493v,10.1021/ol100610v,10.1002/ejoc.201000147,10.1021/ja100783c,10.1021/ol9029534,10.1002/anie.201001028,10.1002/anie.200907359,10.1002/anie.201004426,10.1039/c0cc03107k,10.1002/chem.201000420Kelly11/9/2021
246
42FALSEjacs.0c0028610.1021/jacs.0c00286https://sci-hub.wf/10.1021/jacs.0c00286https://doi.org/10.1021/jacs.0c00286NiC-O ActivationKelly10-FebTRUE4021632020Buchwald, SL
N,N-Diethyl O-Carbamate: Directed Metalation Group and Orthogonal Suzuki-Miyaura Cross-Coupling Partner
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
MIT3/4/2020FALSEFALSEFALSEyyCsp2_ar-Nsp3E-NuOHOTfHHet
N(H)Aryl
Et3NNitrogenNitrogen(neutral)Weak0.53_xx10.1002/anie.202200352,10.1002/anie.20201434010.1002/anie.202200352,10.1021/acscatal.1c05386,10.1002/slct.202103723,10.1021/acscatal.1c05386,10.1070/RCR4999,10.1021/acs.joc.1c01467,10.1055/a-1608-5069,10.1002/anie.202108587,10.3390/molecules26165079,10.1039/d1cc03261e,10.1021/acscatal.1c01929,10.1021/acs.organomet.1c00280,10.1002/anie.202103803,10.1021/acs.joc.1c00681,10.1016/j.rser.2021.111103,10.1016/j.tetlet.2021.153001,10.1002/anie.202016310,10.1002/chem.202004477,10.1002/anie.202012877,10.1002/chem.202003580,10.2174/1570179418666210224124931,10.1016/j.tet.2020.131861,10.1002/anie.202014340,10.1021/acscatal.0c04280,10.1021/jacs.0c09275,10.1021/acs.oprd.0c00367,10.1021/acs.orglett.0c02672,10.1002/chem.202002800,10.6023/cjoc202000059,10.1002/anie.202003359,10.1021/jacs.9b13531,10.2174/138527282499920091411124611/1/2021MAR 42020FALSEFALSEFALSEFALSE14294500
247
24FALSEjacs.0c0133010.1021/jacs.0c01330https://sci-hub.wf/10.1021/jacs.0c01330https://doi.org/10.1021/jacs.0c01330NiC-O ActivationLongTRUE241382020Hong, X
The Quest for the Ideal Base: Rational Design of a Nickel Precatalyst Enables Mild, Homogeneous C-N Cross-Coupling
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Palladium-catalyzed amination reactions using soluble organic bases have provided a solution to the many issues associated with heterogeneous reaction conditions. Still, homogeneous C-N cross-coupling approaches cannot yet employ bases as weak and economical as trialkylamines. Furthermore, organic base-mediated methods have not been developed for Ni(0/II) catalysis, despite some advantages of such systems over those employing Pd-based catalysts. We designed a new air-stable and easily prepared Ni(II) precatalyst bearing an electron-deficient bidentate phosphine ligand that enables the cross-coupling of aryl triflates with aryl amines using triethylamine (TEA) as base. The method is tolerant of sterically congested coupling partners, as well as those bearing base- and nucleophile-sensitive functional groups. With the aid of density functional theory (DFT) calculations, we determined that the electron-deficient auxiliary ligands decrease both the pK(a) of the Ni-bound amine and the barrier to reductive elimination from the resultant Ni(II)-amido complex. Moreover, we determined that the preclusion of Lewis acid-base complexation between the Ni catalyst and the base, due to steric factors, is important for avoiding catalyst inhibition.
Zhejiang Univ3/18/2020Csp3-Csp1E-EOOOMsOMsAlkylAlkyneNo baseNo BaseWeak0.36_10.1021/acs.orglett.1c04268,10.1002/ejoc.202101440,10.1021/jacs.1c10932,10.1021/jacs.1c08695,10.1021/jacs.1c06271,10.1021/jacs.1c03827,10.1021/acs.accounts.1c00050,10.1021/acs.orglett.1c00313,10.1055/s-0040-1705987,10.1021/acsomega.0c04181,10.1021/acscatal.0c03334,10.1021/acs.orglett.0c02722,10.1021/acscatal.0c02514,10.1021/acs.accounts.0c00291,10.1021/acscatal.0c018421/6/2022
248
263FALSEacs.orglett.6b0216610.1021/acs.orglett.6b02166https://sci-hub.wf/10.1021/acs.orglett.6b02166https://doi.org/10.1021/acs.orglett.6b02166NiC-H ActivationGerryTRUE861#N/A2016
Li, PH; Wang, L
Nickel-Catalyzed Site-Selective C-H Bond Difluoroalkylation of 8-Aminoquinolines on the C5-PositionORG LETT
A simple and efficient protocol for nickel-catalyzed regioselective C-H bond difluoroalkylation of 8-aminoquinoline scaffolds with functionalized difluoromethyl bromides was developed. The reaction has broad substrate scope and provides a facile and useful access to the corresponding C5-functionalized difluoromethylated quinolines in good to excellent yields.
Huaibei Normal Univ10/7/2016yCsp3-Csp2_arE-NuXHBrHAlkylArylKHCO3Ionic-HCO3_xxx10.1039/d1cy01254a,10.1016/j.cclet.2020.09.044,10.1002/adsc.202001614,10.1002/ajoc.202000686,10.1002/adsc.202001053,10.1055/s-0040-1707863,10.1055/a-1337-5416,10.1021/acs.joc.0c02114,10.1039/d0cc05491g,10.1002/chem.202003416,10.1039/d0qo00567c,10.1039/d0cc00014k,10.1007/s41061-020-00303-9,10.1055/s-0039-1691579,10.1002/ejoc.201901883,10.1002/adsc.201901158,10.1016/j.catcom.2019.105832,10.1021/acs.orglett.9b03923,10.1039/c9ob02235j,10.1002/ejoc.201901471,10.1002/ajoc.201900624,10.1021/acs.joc.9b00942,10.1002/slct.201901177,10.1002/ajoc.201900293,10.1021/acs.orglett.9b01629,10.1002/slct.201900664,10.1039/c9cy00009g,10.1002/ejoc.201900092,10.1002/adsc.201801246,10.1039/c8ob02942c,10.1002/ejoc.201801058,10.1002/slct.201802644,10.1016/j.tet.2018.09.048,10.1055/s-0037-1610212,10.1021/acs.joc.8b01658,10.1021/acs.joc.8b01635,10.1039/c8cs00201k,10.1021/acs.orglett.8b02451,10.1002/asia.201800504,10.1016/j.catcom.2018.05.021,10.1039/c8sc01221k,10.1021/acs.orglett.8b01395,10.1002/ajoc.201800276,10.1055/s-0037-1610130,10.1039/c8qo00229k,10.1002/ejoc.201800389,10.1039/c8ob00581h,10.1039/c8ob00537k,10.1016/j.tetlet.2018.02.077,10.1039/c7ob03059b,10.1021/acs.joc.8b00068,10.1002/adsc.201701555,10.1021/acs.orglett.7b03955,10.1039/c8ra00761f,10.1039/c8ra07647b,10.1016/j.tetlet.2017.11.037,10.6023/cjoc201705041,10.1002/ejoc.201701150,10.1002/chem.201702311,10.1021/acs.orglett.7b02823,10.1055/s-0036-1588420,10.1055/s-0036-1588160,10.1002/slct.201701388,10.1002/adsc.201700391,10.1002/adsc.201700471,10.1002/adsc.201700186,10.1039/c7qo00211d,10.1055/s-0036-1588493,10.6023/cjoc201703020,10.1039/c7cc02601c,10.1039/c6qo00655h,10.1007/s10562-017-2021-9,10.1039/c6qo00765a,10.1002/cjoc.201600784,10.1039/c6ob02375d,10.1002/slct.201601917,10.1039/c7ra11363c,10.1039/c7ra09053f,10.1039/c6qo00590j,10.1039/c6ob02224c,10.1021/acs.orglett.6b02998,10.1021/acs.orglett.6b028481/5/2022
249
294FALSEjacs.0c0280510.1021/jacs.0c02805https://sci-hub.wf/10.1021/jacs.0c02805https://doi.org/10.1021/jacs.0c02805NiC-O ActivationxWilliam7-JunTRUE531452020Doyle, AG
Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Cross-electrophile coupling reactions of two Csp(3)-X bonds remain challenging. Herein we report an intramolecular nickel-catalyzed cross-electrophile coupling reaction of 1,3-diol derivatives. Notably, this transformation is utilized to synthesize a range of mono- and 1,2-disubstituted alkylcyclopropanes, including those derived from terpenes, steroids, and aldol products. Additionally, enantioenriched cyclopropanes are synthesized from the products of proline-catalyzed and Evans aldol reactions. A procedure for direct transformation of 1,3-diols to cyclopropanes is also described. Calculations and experimental data are consistent with a nickel-catalyzed mechanism that begins with stereoablative oxidative addition at the secondary center.
4/22/2022Csp3-Csp3-ring(s)E-EOX
dimethoxymethanol
ClAlkyl
Csp3-(Het)(Ar)
No baseNo Base6/15/2022
250
40FALSEjacs.0c0467010.1021/jacs.0c04670https://sci-hub.wf/10.1021/jacs.0c04670https://doi.org/10.1021/jacs.0c04670NiC-O ActivationLongTRUE391382020Weix, DJ
Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Methylation of organohalides represents a valuable transformation, but typically requires harsh reaction conditions or reagents. We report a radical approach for the methylation of (hetero)aryl chlorides using nickel/photoredox catalysis wherein trimethyl orthoformate, a common laboratory solvent, serves as a methyl source. This method permits methylation of (hetero)aryl chlorides and acyl chlorides at an early and late stage with broad functional group compatibility. Mechanistic investigations indicate that trimethyl orthoformate serves as a source of methyl radical via beta-scission from a tertiary radical generated upon chlorine-mediated hydrogen atom transfer.
Univ Wisconsin6/17/2020TRUEFALSEFALSEyCsp2_ar-Csp2_arE-EOOOTfOTsArylArylNo baseNo BaseWeak0.53_xx10.1021/jacs.0c0699510.1002/adsc.202101388,10.1021/acscatal.1c05144,10.1021/jacs.1c10907,10.1039/d1qo01406d,10.1021/acs.joc.1c00260,10.1039/d1cc05006k,10.1039/d1ob01874d,10.1021/acscatal.1c02307,10.1039/d1cy01219c,10.1021/acscatal.1c02952,10.1055/a-1608-5693,10.1039/d1cc03261e,10.1016/j.chempr.2021.06.007,10.1039/c9cs00571d,10.1021/jacs.1c04215,10.1021/acscatal.1c01416,10.1055/a-1503-6330,10.1002/ejoc.202100115,10.1016/j.rser.2021.111103,10.1021/acscatal.1c01102,10.1021/acs.orglett.1c00313,10.1039/d0sc06586b,10.1002/chem.202004437,10.1055/a-1349-3543,10.2174/1570179418666210224124931,10.1021/acscatal.0c04713,10.1021/acs.orglett.0c03782,10.1021/acscatal.0c03903,10.1021/jacs.0c06995,10.1021/acs.orglett.0c0216511/11/2021JUN 172020FALSEFALSEFALSEFALSE1422410634
251
266FALSEjacs.5b0250310.1021/jacs.5b02503https://sci-hub.wf/10.1021/jacs.5b02503https://doi.org/10.1021/jacs.5b02503NiC-N ActivationKelly17-FebTRUE1004452015Doyle, AG
Electron-Deficient Olefin Ligands Enable Generation of Quaternary Carbons by Ni-Catalyzed Cross-Coupling
J AM CHEM SOC
A Ni-catalyzed Negishi cross-coupling with 1,1-disubstituted styrenyl aziridines has been developed. This method delivers valuable beta-substituted phenethyl-amines via a challenging reductive elimination that affords a quaternary carbon. A novel electron-deficient olefin ligand, Fro-DO, proved crucial for achieving high rates and chemoselectivity for C-C bond formation over beta-H elimination. This ligand is easy to access, is stable, and presents a modular framework for reaction discovery and optimization. We expect that these attributes, combined with the fact that the ligands impart distinct electronic properties to a metal, will support the invention of new transformations not previously possible using established ligands.
Princeton Univ5/6/2015TRUETRUEFALSECsp3-Csp3-ring(s)E-NuNZn
N(Ring-Opening)
ZnXAlkylBenzylNo baseNo Base_x10.1021/jacs.7b03448,10.1021/jacs.1c03898,10.1021/jacs.6b08075,10.1002/anie.20170552110.1039/d1sc05605k,10.1021/jacs.1c11503,10.1039/d1sc05451a,10.3390/molecules26195947,10.1021/acs.orglett.1c02514,10.1021/jacs.1c05281,10.1021/acs.orglett.1c01821,10.1021/jacs.1c03898,10.1039/d1cc01734a,10.1021/acs.orglett.1c01077,10.1002/adsc.202100195,10.1039/d1qo00264c,10.1021/acs.organomet.0c00775,10.1039/d0cs01107j,10.1055/a-1344-6040,10.1021/acs.inorgchem.0c02831,10.1002/adsc.202001235,10.1021/acscatal.0c03857,10.1021/acscatal.0c03341,10.1021/acscatal.0c03334,10.1021/acs.chemrev.9b00682,10.1039/d0ob00257g,10.1002/ejoc.202000280,10.1021/acscatal.0c01199,10.1021/jacs.0c02237,10.1002/anie.201915454,10.1021/acs.joc.9b02603,10.1039/c9cc07072a,10.1039/c9qo01033e,10.1021/acscatal.9b03620,10.1039/c9sc02507c,10.1021/acs.joc.9b01556,10.1021/acs.joc.9b01713,10.1039/c9cc90354b,10.1002/anie.201906781,10.1002/adsc.201900028,10.1021/acscatal.9b01347,10.1021/acscombsci.9b00076,10.1021/jacs.9b05934,10.1002/chem.201902009,10.1021/acscatal.9b01620,10.1002/chem.201901128,10.1021/acscatal.9b01191,10.1002/adsc.201801545,10.1016/j.ejmech.2018.12.002,10.1021/acs.organomet.8b00720,10.1021/jacs.8b11942,10.1021/acs.orglett.8b03309,10.1021/acsomega.8b03168,10.1039/c8cc07093h,10.1007/s11030-018-9848-x,10.1021/jacs.8b09473,10.1039/c8qo00632f,10.1021/acscatal.8b02187,10.1021/acs.orglett.8b01394,10.1021/acs.orglett.8b00507,10.1039/c8cc00001h,10.1021/acs.orglett.7b03747,10.1021/jacs.7b10855,10.1039/c8ra06354k,10.1055/s-0036-1590893,10.6023/cjoc201702033,10.1002/anie.201705521,10.1021/jacs.7b06723,10.1021/acs.orglett.7b00878,10.1007/s10593-017-2080-2,10.1002/pola.28519,10.1021/jacs.7b03448,10.1021/acs.orglett.6b03430,10.1071/CH16580,10.1021/jacs.6b08075,10.1055/s-0035-1562503,10.1002/chem.201602572,10.1021/acscatal.5b02718,10.1002/anie.201510558,10.1039/c6cc04410g,10.1039/c6sc01120a,10.1039/c5cs00534e,10.1039/c6qo00164e,10.1021/acs.chemrev.5b00386,10.1002/ejoc.201501058,10.1021/jacs.5b0625511/2/2021MAY 62015FALSEFALSEFALSEFALSE137175638
252
275FALSEjacs.0c0690410.1021/jacs.0c06904https://sci-hub.wf/10.1021/jacs.0c06904https://doi.org/10.1021/jacs.0c06904NiC-O ActivationGerry14-MarTRUE181172020
Rousseaux, SAL
Sulfonate Versus Sulfonate: Nickel and Palladium Multimetallic Cross-Electrophile Coupling of Aryl Triflates with Aryl Tosylates
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
While phenols are frequent and convenient aryl sources in cross-coupling, typically as sulfonate esters, the direct cross-Ullmann coupling of two different sulfonate esters is unknown. We report here a general solution to this challenge catalyzed by a combination of Ni and Pd with Zn reductant and LiBr as an additive. The reaction has broad scope, as demonstrated in 33 examples (65% +/- 11% average yield). Mechanistic studies show that Pd strongly prefers the aryl triflate, the Ni catalyst has a small preference for the aryl tosylate, aryl transfer between catalysts is mediated by Zn, and Pd improves yields by consuming arylzinc intermediates.
7/29/2020Csp3-Csp2_arE-NuOZn
OC(S)N(Ph)Bz
ZnXAlkylAryl#N/ANo BaseMedium0.31_10.1021/acs.orglett.1c04074,10.1021/acs.orglett.1c03674,10.6023/cjoc202106021,10.1039/d1cc02930d,10.1021/jacs.1c04254,10.1021/acs.joc.1c00473,10.1039/d0cs01107j,10.1002/anie.202014991,10.1021/acs.orglett.0c04039,10.1021/acs.orglett.1c04074,10.1016/j.jfluchem.2020.109652,10.1039/d0cc05895e,10.1021/acs.orglett.0c023033/15/2022
253
268FALSEchem.20160220210.1002/chem.201602202https://sci-hub.wf/10.1002/chem.201602202https://doi.org/10.1002/chem.201602202NiC-N ActivationLongTRUE9010#N/A2016Szostak, M
Efficient Synthesis of Diaryl Ketones by Nickel-Catalyzed Negishi Cross-Coupling of Amides by Carbon-Nitrogen Bond Cleavage at Room Temperature Accelerated by a Solvent EffectCHEM-EUR J
The first Negishi cross-coupling of amides for the synthesis of versatile diaryl ketones by selective C-N bond activation under exceedingly mild conditions is reported. The cross-coupling was accomplished with bench-stable, inexpensive precatalyst [Ni(PPh3)(2)Cl-2] that shows high functional-group tolerance and enables the synthesis of highly functionalized diaryl ketone motifs. The coupling occurred with excellent chemoselectivity favoring the ketone (cf. biaryl) products. Notably, this process represents the mildest conditions for amide N-C bond activation accomplished to date (room temperature, <10min). Considering the versatile role of polyfunctional biaryl ketone linchpins in modern organic synthesis, availability, and excellent functional-group tolerance of organozinc reagents, this strategy provides a new platform for amide N-C bond/organozinc cross-coupling under mild conditions.
Rutgers State Univ7/18/2016TRUETRUEFALSECsp2-Csp2_arE-NuNZn
piperidine-2,6-dione
ZnX
Carbonyl
ArylNo baseNo BaseE-H_xxAdded by Long10.1055/s-0036-1588845,10.1021/acs.orglett.6b02952,10.1002/chem.201702867,10.1021/jacs.0c06904,10.1021/acs.orglett.7b00831,10.1021/acscatal.7b01444,10.1021/acs.orglett.8b01021,10.1039/c7sc01980g,10.1021/acscatal.7b03688,10.1002/anie.20160785610.1002/anie.202201142,10.1055/a-1679-8205,10.1039/c9cs00571d,10.1002/cctc.202100672,10.1039/d1nj01348c,10.6023/cjoc202009048,10.1021/acs.orglett.0c03260,10.1021/acscatal.0c03341,10.1055/s-0040-1706550,10.1055/s-0040-1707133,10.1016/j.tetlet.2020.152444,10.1021/acscatal.0c03334,10.1021/jacs.0c06904,10.1021/acs.orglett.0c00885,10.1021/acscatal.9b05159,10.1055/s-0039-1690764,10.1021/acs.orglett.9b03434,10.1002/ejoc.201901396,10.1177/1747519819873514,10.1002/adsc.201900819,10.1039/c9cc05763c,10.1021/acs.joc.9b01699,10.1002/adsc.201900485,10.1055/s-0037-1611549,10.1002/ejoc.201900531,10.1039/c9nj01748h,10.1080/00397911.2019.1594306,10.1002/ejoc.201900517,10.1002/adsc.201801577,10.1021/acs.jchemed.8b00489,10.1021/acs.organomet.8b00720,10.1002/asia.201801317,10.3390/catal9010053,10.1039/c8ra07447j,10.3390/molecules23102681,10.3390/molecules23102615,10.1021/acs.oprd.8b00182,10.1021/acscatal.8b01380,10.1002/ejoc.201800109,10.1016/j.tetlet.2018.05.003,10.1021/acs.orglett.8b01028,10.1021/acs.orglett.8b01021,10.1021/acs.joc.8b00160,10.1016/j.tetlet.2018.01.097,10.1002/chem.201800336,10.1021/acs.orglett.8b00086,10.1039/c7ob02874a,10.1021/acscatal.7b03688,10.1007/s11426-017-9025-1,10.1021/acs.organomet.7b00446,10.1002/chem.201702867,10.1039/c7sc02692g,10.1039/c7sc01980g,10.1021/acs.orglett.7b01623,10.1055/s-0036-1588845,10.1002/chem.201702608,10.1021/acs.orglett.7b01575,10.1021/acscatal.7b01444,10.1021/acs.orglett.7b01194,10.1021/acs.orglett.7b01199,10.1021/acs.joc.7b00570,10.1002/anie.201703174,10.1002/chem.201605012,10.1021/acs.orglett.7b00831,10.1021/acs.orglett.7b00796,10.1021/acs.orglett.7b00429,10.1021/acs.orglett.7b00683,10.1021/acs.orglett.7b00373,10.1021/acscatal.6b03616,10.1038/s41570-017-0025,10.1039/c7ob00086c,10.1021/acs.joc.6b02846,10.1021/acscatal.6b03277,10.1021/jacs.6b12329,10.1021/acs.joc.6b02294,10.1002/adsc.201600555,10.1002/anie.201607856,10.1021/acs.orglett.6b02952,10.1021/acscatal.6b02323,10.1055/s-0036-1588080,10.1002/chem.201603543,10.1021/acs.orglett.6b01836,10.1002/chem.201602717,10.1021/acscatal.6b01360,10.1039/c6ob01621a12/22/2021
254
269FALSEacs.orglett.6b0295210.1021/acs.orglett.6b02952https://sci-hub.wf/10.1021/acs.orglett.6b02952https://doi.org/10.1021/acs.orglett.6b02952NiC-N ActivationLongTRUE8910#N/A2016Szostak, M
Nickel-Catalyzed Diaryl Ketone Synthesis by N-C Cleavage: Direct Negishi Cross-Coupling of Primary Amides by Site-Selective N,N-Di-Boc ActivationORG LETT
A general Negishi acylation of primary amides enabled by a combination of site-selective N,N-di-Boc activation and nickel catalysis is reported for the first time. The reaction is promoted by a bench-stable, inexpensive Ni catalyst. The reaction shows excellent functional group compatibility, affording functionalized diaryl ketones by selective N-C cleavage. Most notably, this protocol represents the first amide cross-coupling by direct metal insertion of simple and readily available primary amides. The overall strategy by N,N-di-Boc activation/metal insertion is suitable for a broad range of coupling protocols via acylmetals. Mechanistic experiments suggest high reactivity of N,N-di-Boc activated 1 degrees amides in direct amide C-N cross-couplings.
Rutgers State Univ11/18/2016TRUETRUEFALSECsp2-Csp2_arE-NuNZn
N(Boc)(Boc)
ZnX
Carbonyl
ArylNo baseNo Base_xxOrganic Letter with high citation10.1021/jacs.7b06191,10.1002/chem.201702867,10.1021/acs.orglett.9b00242,10.1021/acscatal.7b01444,10.1021/jacs.7b12865,10.1021/acscatal.7b03688,10.1055/s-0036-1588845,10.1021/acs.orglett.8b01021,10.1021/acs.orglett.7b00831,10.1039/c7sc01980g10.1055/a-1679-8205,10.1002/anie.202114731,10.1002/chem.202103486,10.1002/chem.202101880,10.1002/aoc.6368,10.1039/c9cs00571d,10.1002/cctc.202100672,10.1039/d1nj01348c,10.1021/acs.orglett.0c03260,10.1055/s-0040-1706550,10.1021/acscatal.0c03334,10.1039/d0qo00797h,10.1016/j.trechm.2020.08.001,10.1002/chem.202001816,10.1002/anie.202004441,10.1002/ejoc.202000575,10.1002/aoc.5636,10.1021/acs.orglett.0c00885,10.1002/asia.202000117,10.1002/ejoc.201901730,10.1021/acs.joc.9b02561,10.1021/acs.orglett.9b03434,10.1002/ejoc.201901396,10.1177/1747519819873514,10.1002/adsc.201900819,10.1021/acs.orglett.9b02899,10.1039/c9cc05763c,10.1021/acs.joc.9b01699,10.1021/acs.joc.9b01103,10.1002/adsc.201900485,10.1039/c9nj01748h,10.1039/c9qo00106a,10.1002/adsc.201801577,10.1021/acs.jchemed.8b00489,10.3390/molecules24071234,10.1002/chem.201802635,10.1021/acs.orglett.9b00242,10.1021/acs.organomet.8b00720,10.1002/asia.201801317,10.3390/catal9010053,10.1039/c8ra07447j,10.1039/c8ob01832d,10.1039/c8cs00335a,10.1039/c8qo00591e,10.3390/molecules23102412,10.1021/acs.oprd.8b00182,10.1039/c8nj01585f,10.1002/ejoc.201800109,10.1016/j.tetlet.2018.05.003,10.1021/acs.orglett.8b01021,10.1021/acs.joc.8b00649,10.1021/acs.joc.8b00160,10.1016/j.tetlet.2018.01.097,10.1021/jacs.7b12865,10.1021/acscatal.7b03688,10.1055/s-0036-1590932,10.1021/jacs.7b11309,10.1021/acscatal.7b02599,10.1021/acs.orglett.7b03191,10.1039/c7cc07529d,10.1021/jacs.7b09482,10.1007/s11426-017-9025-1,10.1039/c7cs00182g,10.1021/acscatal.7b02859,10.1021/acscatal.7b02540,10.1002/chem.201702867,10.1039/c7sc01980g,10.1021/jacs.7b06191,10.1055/s-0036-1588845,10.1002/chem.201702608,10.1021/acs.orglett.7b01575,10.1021/acscatal.7b01444,10.1021/acs.orglett.7b01194,10.1021/acs.orglett.7b01199,10.1002/anie.201703174,10.1002/chem.201605012,10.1021/acs.orglett.7b00831,10.1021/acs.orglett.7b00796,10.1021/acs.orglett.7b00429,10.1021/acs.orglett.7b00447,10.1021/acs.orglett.7b00683,10.1021/acs.orglett.7b00373,10.1021/acscatal.6b03616,10.1039/c7ob00086c,10.1021/acscatal.6b0327711/4/2021
255
26FALSEjacs.0c0699510.1021/jacs.0c06995https://sci-hub.wf/10.1021/jacs.0c06995https://doi.org/10.1021/jacs.0c06995NiC-O ActivationLongTRUE191122020Neufeldt, SR
The Cyclopropane Ring as a Reporter of Radical Leaving-Group Reactivity for Ni-Catalyzed C(sp(3))-O Arylation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
The ability to understand and predict reactivity is essential for the development of new reactions. In the context of Ni-catalyzed C(sp(3))-O functionalization, we have developed a unique strategy employing activated cyclopropanols to aid the design and optimization of a redox-active leaving group for C(sp(3))-O arylation. In this chemistry, the cyclopropane ring acts as a reporter of leaving-group reactivity, since the ring-opened product is obtained under polar (2e) conditions, and the ringclosed product is obtained under radical (1e) conditions. Mechanistic studies demonstrate that the optimal leaving group is redox-active and are consistent with a Ni(I)/Ni(III) catalytic cycle. The optimized reaction conditions are also used to synthesize a number of arylcyclopropanes, which are valuable pharmaceutical motifs.
Montana State Univ
9/9/2020TRUEFALSEFALSEyyCsp2_ar-Csp2_arE-NuOBOTsB(nep)ArylArylK3PO4Ionic-PO4Weak0.36_xx10.1021/jacs.1c0839910.1002/anie.202114365,10.1021/acscatal.1c04895,10.1021/jacs.1c08399,10.1039/d1qo01106e,10.1002/chem.202101484,10.1021/acs.organomet.1c00280,10.1021/acscatal.1c02146,10.1021/acs.orglett.1c01280,10.1021/acscatal.1c01201,10.1055/a-1503-6330,10.1039/d1cy00374g,10.1021/acscatal.0c04287,10.1002/chem.202004437,10.1055/a-1349-3543,10.1055/a-1306-322811/16/2021SEP 92020FALSEFALSEFALSEFALSE1423615454
256
271FALSEjacs.9b0011110.1021/jacs.9b00111https://sci-hub.wf/10.1021/jacs.9b00111https://doi.org/10.1021/jacs.9b00111NiC-N ActivationElaineTRUE257272019Watson, MP
Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl-Alkyl Cross-Couplings
J AM CHEM SOC
A Negishi cross-coupling of alkylpyridinium salts and alkylzinc halides has been developed. This is the first example of alkyl-alkyl bond formation via cross-coupling of an alkyl amine derivative with an unactivated alkyl group, and allows both primary and secondary alkylpyridinium salts to react with primary alkylzinc halides with high functional group tolerance. When combined with formation of the pyridinium salts from primary amines, this method enables the non-canonical transformation of NH2 groups into a wide range of alkyl substituents with broad functional group tolerance.
Univ Delaware2/13/2019TRUETRUEFALSECsp2_ar-Csp3E-NuNZn
Triphenylpyridinium+BF4-
ZnXHetAlkylNo baseNo Base_x10.1021/acs.orglett.9b01016,10.1038/s41467-021-25222-1,10.1021/acs.orglett.9b04497,10.1021/acs.orglett.9b01014,10.1002/anie.202002271,10.1126/sciadv.aaw9516,10.1039/c9sc00783k10.1055/s-0040-1719881,10.1039/d1cs01084k,10.1021/jacs.1c12350,10.1021/jacs.1c09412,10.1021/jacs.1c12622,10.1016/j.tet.2021.132605,10.1021/acs.orglett.1c03870,10.1021/jacs.1c10150,10.1038/s41467-021-27060-7,10.1002/anie.202112454,10.1021/acs.orglett.1c03194,10.1021/jacs.1c09779,10.1002/adsc.202100940,10.3390/molecules26195947,10.1055/s-0040-1707817,10.1002/ajoc.202100438,10.1021/acs.joc.1c01555,10.1021/acs.orglett.1c02458,10.1038/s41467-021-25222-1,10.1021/acs.orglett.1c01959,10.1021/acs.joc.1c01076,10.1021/acscatal.1c01860,10.1002/cctc.202100672,10.1021/acs.orglett.1c01716,10.1039/d1sc01217g,10.1021/acscatal.1c01416,10.1016/j.tetlet.2021.153071,10.1038/s41586-021-03448-9,10.1039/d1sc00986a,10.1021/acs.orglett.1c00178,10.1002/anie.202016811,10.1021/acs.orglett.1c00346,10.1039/d0qo01479f,10.1039/d0cc07632e,10.1002/ejoc.202001193,10.1039/d0ob01807d,10.1016/j.tet.2020.131811,10.1021/jacs.0c11172,10.1021/acs.joc.0c01928,10.1021/acscatal.0c03341,10.1039/d0cc05633b,10.1021/jacs.0c08595,10.6023/A20070335,10.1007/s11426-020-9838-x,10.1002/ejic.202000782,10.1039/d0cc04062b,10.1021/acs.joc.0c01274,10.1021/acs.orglett.0c01592,10.1002/anie.202006048,10.1002/adsc.202000457,10.1021/acs.oprd.0c00104,10.1021/acs.orglett.0c01284,10.1002/anie.202002271,10.1002/anie.201914555,10.1021/acs.orglett.0c00554,10.1002/anie.201911660,10.1039/d0sc00225a,10.1002/chem.202000412,10.1021/acs.orglett.9b04327,10.1021/acs.orglett.9b04497,10.1021/jacs.9b12167,10.1021/jacs.9b12343,10.1055/s-0039-1690703,10.1021/acs.joc.9b02538,10.1039/c9ob02107h,10.1039/c9cc08333b,10.1002/chem.201905048,10.1021/acs.orglett.9b03899,10.1021/acs.joc.9b02323,10.1021/acs.orglett.9b03284,10.1021/jacs.9b07489,10.1021/acscatal.9b03084,10.1039/c9cc05385a,10.1021/acs.orglett.9b02643,10.1038/s41467-019-12216-3,10.1002/adsc.201900576,10.1021/acs.orglett.9b02534,10.1021/acscatal.9b02440,10.1002/adsc.201900803,10.1002/anie.201903890,10.1002/chem.201901397,10.1126/sciadv.aaw9516,10.1038/s41929-019-0292-9,10.1021/jacs.9b02312,10.1021/acs.orglett.9b01097,10.1039/c9sc00783k,10.1021/jacs.9b02238,10.1021/acs.orglett.9b01014,10.1021/acs.orglett.9b0101611/8/2021FEB 132019FALSEFALSEFALSEFALSE14162257
257
285FALSEjacs.0c1047110.1021/jacs.0c10471https://sci-hub.wf/10.1021/jacs.0c10471https://doi.org/10.1021/jacs.0c10471NiC-O ActivationxJustin28-MayTRUE501#N/A2020Huo, HH
Small Phosphine Ligands Enable Selective Oxidative Addition of Ar-O over Ar-Cl Bonds at Nickel(0)
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Current methods for Suzuki-Miyaura couplings of nontriflate phenol derivatives are limited by their intolerance of halides including aryl chlorides. This is because Ni(0) and Pd(0) often undergo oxidative addition of organohalides at a similar or faster rate than most Ar-O bonds. DFT and stoichiometric oxidative addition studies demonstrate that small phosphines, in particular PMe3, are unique in promoting preferential reaction of Ni(0) with aryl tosylates and other C-O bonds in the presence of aryl chlorides. This selectivity was exploited in the first Ni-catalyzed C-O-selective Suzuki-Miyaura coupling of chlorinated phenol derivatives where the oxygen-containing leaving group is not a fluorinated sulfonate such as triflate. Computational studies suggest that the origin of divergent selectivity between PMe3 and other phosphines differs from prior examples of ligand-controlled chemodivergent cross-couplings. PMe3 effects selective reaction at tosylate due to both electronic and steric factors. A close interaction between nickel and a sulfonyl oxygen of tosylate during oxidative addition is critical to the observed selectivity.
11/11/2020Csp3-Csp3E-NuOHOHHAlkylAlkylNa2HPO4Strong-0.816/1/2022
258
37FALSEjacs.0c1246210.1021/jacs.0c12462https://sci-hub.wf/10.1021/jacs.0c12462https://doi.org/10.1021/jacs.0c12462NiC-O ActivationShihongTRUE47402021Shu, XZ
Direct Enantioselective C(sp(3))-H Acylation for the Synthesis of alpha-Amino Ketones
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
A direct enantioselective acylation of alpha-amino C(sp(3))-H bonds with carboxylic acids has been achieved via the merger of transition metal and photoredox catalysis. This straightforward protocol enables cross-coupling of a wide range of carboxylic acids, one class of feedstock chemicals, with readily available N-alkyl benzamides to produce highly valuable alpha-amino ketones in high enantioselectivities under mild conditions. The synthetic utility of this method is further demonstrated by gram scale synthesis and application to late-stage functionalization. This method provides an unprecedented solution to address the challenging stereocontrol in metallaphotoredox catalysis and C(sp(3))-H functionalization. Mechanistic studies suggest the alpha-C(sp(3))-H bond of the benzamide coupling partner is cleavage by photocatalytically generated bromine radicals to form a-amino alkyl radicals, which subsequently engages in nickel-catalyzed asymmetric acylation.
Lanzhou Univ1/13/2021TRUETRUEFALSECsp3-Csp2_arE-EOOOHOAcAlkylArylNo baseNo BaseStrong-0.81_xx10.1021/acscatal.1c05208,10.1021/jacs.0c13093,10.1021/acscatal.1c05208,10.1002/anie.20211455610.1002/anie.202200215,10.1002/anie.202116775,10.1021/acs.orglett.2c00207,10.1002/asia.202101370,10.1021/acs.oprd.1c00410,10.1021/acscatal.1c05530,10.1021/acs.oprd.1c00410,10.1021/acscatal.1c04533,10.1021/acs.orglett.1c03991,10.1021/acscatal.1c05208,10.1021/acs.orglett.1c03674,10.1039/d1qo01614h,10.1002/anie.202114556,10.1021/acscatal.1c04239,10.1002/anie.202112876,10.6023/cjoc202106021,10.1039/d1ob01874d,10.1021/acs.orglett.1c02893,10.1021/acs.joc.1c01790,10.1021/acs.orglett.1c02874,10.1021/jacs.1c08695,10.1021/jacs.1c05661,10.1038/s41586-021-03920-6,10.1021/jacs.1c05670,10.1021/acs.oprd.1c00241,10.1039/d1cc03261e,10.1039/c9cs00571d,10.1021/jacs.1c04254,10.1055/a-1467-2432,10.1021/jacs.1c00618,10.1055/a-1406-0484,10.1021/jacs.0c13093 Long 11/5/2021JAN 132021FALSEFALSEFALSEFALSE1431513
259
264FALSEjacs.0c1309310.1021/jacs.0c13093https://sci-hub.wf/10.1021/jacs.0c13093https://doi.org/10.1021/jacs.0c13093NiC-O ActivationxGerry5-MarTRUE58222021Li, C
Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Catalytic transformation of alcohols via metal-catalyzed cross-coupling reactions is very important, but it typically relies on a multistep procedure. We here report a dynamic kinetic cross-coupling approach for the direct functionalization of alcohols. The feasibility of this strategy is demonstrated by a nickel-catalyzed cross-electrophile arylation reaction of benzyl alcohols with (hetero)aryl electrophiles. The reaction proceeds with a broad substrate scope of both coupling partners. The electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles (e.g., Ar-OTf, Ar-I, Ar-Br, and inert Ar-Cl) all coupled well. Most of the functionalities, including aldehyde, ketone, amide, ester, nitrile, sulfone, furan, thiophene, benzothiophene, pyridine, quinolone, Ar-SiMe3, Ar-Bpin, and Ar-SnBu3, were tolerated. The dynamic nature of this method enables the direct arylation of benzylic alcohol in the presence of various nucleophilic groups, including nonactivated primary/secondary/tertiary alcohols, phenols, and free indoles. It thus offers a robust alternative to existing methods for the precise construction of diarylmethanes. The synthetic utility of the method was demonstrated by a concise synthesis of biologically active molecules and by its application to peptide modification and conjugation. Preliminary mechanistic studies revealed that the reaction of in situ formed benzyl oxalates with nickel, possibly via a radical process, is an initial step in the reaction with aryl electrophiles.
3/10/2021Csp3-Csp2_arE-EOXOHBrAlkylAryl#N/ANo BaseStrong-0.81_10.1021/acscatal.1c05208,10.1021/acscatal.1c0520810.1002/anie.202112533,10.1021/acs.oprd.1c00410,10.1021/acs.iecr.1c04508,10.1021/jacs.1c12203,10.1021/acscatal.1c05530,10.1021/acs.oprd.1c00410,10.1021/acscatal.1c05208,10.1002/anie.202115178,10.1021/acs.orglett.1c03674,10.1021/jacs.1c09341,10.1021/jacs.1c10932,10.1021/jacs.1c11170,10.1016/j.chempr.2021.10.023,10.1021/acs.orglett.1c03500,10.1039/d1cc04656j,10.1021/acscatal.1c04239,10.1021/acs.orglett.1c02893,10.1016/j.chempr.2021.09.006,10.1021/acs.joc.1c01790,10.1021/acs.orglett.1c02738,10.1038/s41467-021-25702-4,10.1021/jacs.1c05661,10.1038/s41586-021-03920-6,10.1039/d1sc04011a,10.1002/anie.202107820,10.1021/acs.oprd.1c00241,10.1055/a-1581-0934,10.1016/j.xcrp.2021.100476,10.1021/jacs.1c04254,10.1002/tcr.2021001423/10/2022
260
275FALSEanie.20151119710.1002/anie.201511197https://sci-hub.wf/10.1002/anie.201511197https://doi.org/10.1002/anie.201511197NiC-H ActivationGerry14-FebTRUE9211892016Chatani, N
Phenyltrimethylammonium Salts as Methylation Reagents in the Nickel-Catalyzed Methylation of C-H Bonds
ANGEW CHEM INT EDIT
Methylation of C(sp(2))-H bonds was achieved through the Ni-II-catalyzed reaction of benzamides with phenyltrimethylammonium bromide or iodide as the source of the methyl group. The reaction has a broad scope and shows high functional-group compatibility. The reaction is also applicable to the methylation of C(sp(3))-H bonds in aliphatic amides.
Osaka Univ2/24/2016TRUEFALSEFALSEyCsp3-Csp2_arE-NuNH
NMe3+I-
HAlkylArylNa2CO3Ionic-CO3E-H_
10.1021/acscatal.7b01058,10.1021/acscatal.6b02003,10.1039/c6qo00149a,10.1038/ncomms12937,10.1021/acs.organomet.6b00201,10.1021/acs.orglett.6b02166,10.1002/ajoc.201700569,10.1021/acs.orglett.6b02236,10.1002/chem.201603436,10.1021/acs.orglett.6b00658,10.1039/d1cc02983e
10.1002/adsc.202101499,10.1016/j.tet.2021.132431,10.1039/d1ob01468d,10.1016/j.tet.2021.132402,10.1021/acs.joc.1c01558,10.1021/acscatal.1c02010,10.1055/a-1581-0934,10.1039/d1cc03589d,10.1021/acs.joc.1c01325,10.1039/d1cc02983e,10.1039/d1qo00759a,10.1039/d1qo00727k,10.1021/acs.organomet.1c00265,10.1039/d0cs00973c,10.1039/d1sc00757b,10.1021/jacs.0c13057,10.1021/acs.joc.0c02992,10.1016/bs.adomc.2021.04.003,10.1021/acs.joc.0c02069,10.1021/acs.orglett.0c03535,10.6023/cjoc202006075,10.1002/anie.202010958,10.1055/s-0039-1691574,10.1002/anie.202004958,10.1039/d0gc01183e,10.1039/d0qo00173b,10.1002/cjoc.201900468,10.1002/chem.202000412,10.1021/jacs.0c00127,10.3390/molecules25051141,10.1039/c9ob02667c,10.1016/j.catcom.2019.105835,10.1039/c9ob02107h,10.1038/s41557-019-0358-y,10.1002/ejoc.201901211,10.1021/jacs.9b07857,10.1002/anie.201906658,10.1002/tcr.201800093,10.1002/ejoc.201900918,10.1021/acs.joc.9b01204,10.1016/j.trechm.2019.06.002,10.1038/s41929-019-0300-0,10.1039/c9ob00449a,10.1002/anie.201806629,10.1039/c9ob00243j,10.1021/acscatal.9b00218,10.1039/c8sc05063e,10.1021/acs.orglett.9b00351,10.1002/chem.201803642,10.1039/c8qo01310a,10.1021/acs.chemrev.8b00507,10.1021/acs.joc.8b02701,10.1021/acscatal.8b03770,10.1021/jacs.8b07708,10.1039/c8ob01712c,10.1002/anie.201804794,10.6023/cjoc201803013,10.1039/c8qo00438b,10.1002/anie.201712618,10.1039/c7sc04604a,10.1002/ajoc.201700569,10.1021/acs.orglett.7b02968,10.1002/ijch.201700044,10.1002/anie.201706237,10.1002/asia.201701132,10.1039/c7sc01750b,10.1055/s-0036-1589010,10.1039/c7cc05011a,10.1021/jacs.7b03548,10.1021/acscatal.7b01058,10.1021/acs.orglett.7b00116,10.1039/c6gc03355e,10.1021/acs.organomet.6b00810,10.1071/CH16602,10.1021/acs.orglett.6b02860,10.1021/acscatal.6b02477,10.1002/chem.201603436,10.1021/acs.orglett.6b02166,10.1021/acs.orglett.6b02236,10.1021/acscatal.6b02003,10.1038/ncomms12937,10.1002/chem.201602445,10.1007/s41061-016-0053-z,10.1021/acscatal.6b00964,10.1021/acs.organomet.6b00201,10.1021/acs.orglett.6b00658,10.1039/c6cc07196a,10.1039/c6qo00149a
12/29/2021FEB 242016FALSEFALSEFALSEFALSE5593162
261
282FALSEjacs.1c0566110.1021/jacs.1c05661https://sci-hub.wf/10.1021/jacs.1c05661https://doi.org/10.1021/jacs.1c05661NiC-O ActivationLong5-AprTRUE71152021Newman, SG
Electrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
As alcohols are ubiquitous throughout chemical science, this functional group represents a highly attractive starting material for forging new C-C bonds. Here, we demonstrate that the combination of anodic preparation of the alkoxy triphenylphosphonium ion and nickel-catalyzed cathodic reductive crosscoupling provides an efficient method to construct C(sp(2))-C(sp(3)) bonds, in which free alcohols and aryl bromides-both readily available chemicals.can be directly used as coupling partners. This nickel-catalyzed paired electrolysis reaction features a broad substrate scope bearing a wide gamut of functionalities, which was illustrated by the late-stage arylation of several structurally complex natural products and pharmaceuticals.
9/15/2021Csp3-ring(s)-Csp2_arE-NuOAlOH
Al(iBu)2
BenzylArylTMPNitrogenNitrogen(neutral)Strong-0.8110.1002/anie.202117843,10.1002/anie.202201370,10.1021/jacs.1c111704/15/2022
262
314FALSEjacs.1c0810510.1021/jacs.1c08105https://sci-hub.wf/10.1021/jacs.1c08105https://doi.org/10.1021/jacs.1c08105NiC-O ActivationxWilliam5-JulyTRUE161452021Doyle, AG
Catalytic Aldehyde and Alcohol Arylation Reactions Facilitated by a 1,5-Diaza-3,7-diphosphacyclooctane Ligand
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
We report a catalytic method to access secondary alcohols by the coupling of aryl iodides. Either aldehydes or alcohols can be used as reaction partners, making the transformation reductive or redox-neutral, respectively. The reaction is mediated by a Ni catalyst and a 1,5-diaza-3,7-diphosphacyclooctane. This P2N2 ligand, which has previously been unrecognized in cross-coupling and related reactions, was found to avoid deleterious aryl halide reduction pathways that dominate with more traditional phosphines and NHCs. An interrupted carbonyl-Heck type mechanism is proposed to be operative, with a key 1,2-insertion step forging the new C-C bond and forming a nickel alkoxide that may be turned over by an alcohol reductant. The same catalyst was also found to enable synthesis of ketone products from either aldehydes or alcohols, demonstrating control over the oxidation state of both the starting materials and products.
Csp3-Csp3E-EOX
O(Ring-Opening)
XAlkylAlkylEt3NNitrogenNitrogen(neutral)Weak17/6/2022
263
252FALSEjacs.1c0839910.1021/jacs.1c08399https://sci-hub.wf/10.1021/jacs.1c08399https://doi.org/10.1021/jacs.1c08399NiC-O ActivationGerry21-FebTRUE111#N/A2021Gosselin, F
Ni/Photoredox-Catalyzed Enantioselective Cross-Electrophile Coupling of Styrene Oxides with Aryl Iodides
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
A Ni/photoredox- catalyzed enantioselective reductive coupling of styrene oxides and aryl iodides is reported. This reaction affords access to enantioenriched 2,2-diarylalcohols from racemic epoxides via a stereoconvergent mechanism. Multivariate linear regression (MVLR) analysis with 29 bioxazoline (BiOx) and biimidazoline (BiIm) ligands revealed that enantioselectivity correlates with electronic properties of the ligands, with more electron-donating ligands affording higher ee's. Experimental and computational mechanistic studies were conducted, lending support to the hypothesis that reductive elimination is enantiodetermining and the electronic character of the ligands influences the enantioselectivity by altering the position of the transition state structure along the reaction coordinate. This study demonstrates the benefits of utilizing statistical modeling as a platform for mechanistic understanding and provides new insight into an emerging class of chiral ligands for stereoconvergent Ni and Ni/photoredox cross-coupling.
11/17/2021Csp2-Csp2_arE-NuOBOTsBpinVinylArylIonic-PO4Weak0.36_10.1021/jacs.1c09718,10.1021/jacs.1c09718,10.1021/acs.jpclett.1c04099,10.1021/acs.orglett.1c041232/28/2022
264
255FALSEjacs.1c0850210.1021/jacs.1c08502https://sci-hub.wf/10.1021/jacs.1c08502https://doi.org/10.1021/jacs.1c08502NiC-O ActivationLong24-FebTRUE81#N/A2021Song, SL
Stereoconvergent and -divergent Synthesis of Tetrasubstituted Alkenes by Nickel-Catalyzed Cross-Couplings
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
We report the development of a method to diastereoselectively access tetrasubstituted alkenes via nickel-catalyzed Suzuki-Miyaura cross-couplings of enol tosylates and boronic acid esters. Either diastereomeric product was selectively accessed from a mixture of enol tosylate starting material diastereomers in a convergent reaction by judicious choice of the ligand and reaction conditions. A similar protocol also enabled a divergent synthesis of each product isomer from diastereomerically pure enol tosylates. Notably, high-throughput optimization of the monophosphine ligands was guided by chemical space analysis of the kraken library to ensure a diverse selection of ligands was examined. Stereoelectronic analysis of the results provided insight into the requirements for reactive and selective ligands in this transformation. The synthetic utility of the optimized catalytic system was then probed in the stereoselective synthesis of various tetrasubstituted alkenes, with yields up to 94% and diastereomeric ratios up to 99:1 Z/E and 93:7 E/Z observed. Moreover, a detailed computational analysis and experimental mechanistic studies provided key insights into the nature of the underlying isomerization process impacting selectivity in the cross-coupling.
10/27/2021Csp2_ar-Csp2_arE-NuOBOMsB(OH)2ArylArylIonic-PO4Weak0.36_10.1021/acscatal.1c052083/11/2022
265
12FALSEjacs.1c0979710.1021/jacs.1c09797https://sci-hub.wf/10.1021/jacs.1c09797https://doi.org/10.1021/jacs.1c09797NiC-O ActivationLong13 FebTRUE9142021Cao, ZC
An Accelerated Modular-Orthogonal Ni-Catalyzed Methodology to Symmetric and Nonsymmetric Constitutional Isomeric AB(2) to AB(9) Dendrons Exhibiting Unprecedented Self-Organizing Principles
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Five libraries of natural and synthetic phenolic acids containing five AB(3), ten constitutional isomeric AB(2), one AB(4), and one AB(5) were previously synthesized and reported by our laboratory in 5 to 11 steps. They were employed to construct seven libraries of self-assembling dendrons, by divergent generational, deconstruction, and combined approaches, enabling the discovery of a diversity of supramolecular assemblies including Frank-Kasper phases, soft quasicrystals, and complex helical organizations, some undergoing deracemization in the crystal state. However, higher substitution patterns within a single dendron were not accessible. Here we report three libraries consisting of 30 symmetric and nonsymmetric constitutional isomeric phenolic acids with unprecedented sequenced patterns, including two AB(2), three AB(3), eight AB(4), five AB(5), six AB(6), three AB(7), two AB(8), and one AB(9) synthesized by accelerated modular-orthogonal Ni-catalyzed borylation and cross-coupling. A single etherification step with 4-(n-dodecyloxy)benzyl chloride transformed all these phenolic acids, of interest also for other applications, into self-assembling dendrons. Despite this synthetic simplicity, they led to a diversity of unprecedented self-organizing principles: lamellar structures of interest for biological membrane mimics, helical columnar assemblies from rigid-solid angle dendrons forming Tobacco Mosaic Virus-like assemblies, columnar organizations from adaptable-solid angle dendrons forming disordered micellar-like nonhelical columns, columns from supramolecular spheres, five body-centered cubic phases displaying supramolecular orientational memory, rarely encountered in previous libraries forming predominantly Frank-Kasper phases, and two Frank-Kasper phases. Lessons from these self-organizing principles, discovered within a single generation of self-assembling dendrons, may help elaborate design principles for complex helical and nonhelical organizations of synthetic and biological matter.
Anhui Agr Univ11/10/2021Csp3-Csp2_arE-NuOMg
O(Ring-Opening)
MgXAlkylArylNo baseNo BaseWeak1_x10.1039/d2sc00341d,10.1021/acs.orglett.1c03849,10.1021/acs.orglett.1c03849,10.1021/acs.orglett.1c03484 Long 1/6/2022
266
259FALSEjacs.1c1104410.1021/jacs.1c11044https://sci-hub.wf/10.1021/jacs.1c11044https://doi.org/10.1021/jacs.1c11044NiC-O ActivationGerry2-MarTRUE31172021Guo, C
Nickel-Catalyzed Enantioselective Arylative Activation of Aromatic C-O Bond
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
The pioneering nickel-catalyzed cross-coupling of C-O electrophiles was unlocked by Wenkert in the 1970s; however, the transition-metal-catalyzed asymmetric activation of aromatic C-O bonds has never been reported. Herein the first enantioselective activation of an aromatic C-O bond is demonstrated via the catalytic arylative ring-opening cross-coupling of diarylfurans. This transformation is facilitated via nickel catalysis in the presence of chiral N-heterocyclic carbene ligands, and chiral 2-aryl-2'- hydroxy-1,1'- binaphthyl (ArOBIN) skeletons are delivered axially in high yields with high ee. Moreover, this versatile skeleton can be transformed into various synthetic useful intermediates, chiral catalysts, and ligands by using the CH- and OH-based modifiable sites. This chemistry features mild conditions and good atom economy.
12/15/2021Csp3-Osp2E-NuOH
OCO2Me
HAlkylORNo baseNo BaseMedium0.31_10.1038/s41467-020-20644-9,10.1002/ajoc.202000422,10.1002/anie.202005019,10.1038/s41929-020-0462-9,10.1021/acs.orglett.0c00465,10.1126/science.aaz3855,10.1002/anie.201912408,10.1021/jacs.9b02338,10.1021/jacs.8b11159,10.1021/acs.orglett.8b02325,10.1039/c8ra04481c,10.1002/anie.201703704,10.1002/anie.201703029,10.1002/anie.201604025,10.1002/adsc.201600284,10.1002/anie.201510793,10.1021/acs.chemrev.5b00676,10.1021/jacs.5b08477,10.1002/chem.201502329,10.1021/jacs.5b02212,10.1021/jacs.5b00004,10.1016/j.tetlet.2014.11.112,10.1002/anie.201408199,10.1002/anie.201405857,10.1016/j.ejmech.2014.02.063,10.1002/anie.201307789,10.1021/ja402740q,10.1021/jm301516q,10.1002/anie.201205343,10.1002/anie.201205449,10.1021/jm2010404,10.1002/ejoc.201100044,10.1021/cr100284m,10.1002/anie.201104017,10.1021/ja102436z,10.1055/s-0029-1219365,10.1021/jm9010803,10.1002/anie.200905332,10.1002/ejoc.200900877,10.1002/cctc.200900214,10.1002/anie.200902084,10.1021/ja805635c,10.1021/ja807188s,10.1021/ja805165y,10.1021/jm8001795,10.1021/ja802704j,10.1039/b710668h,10.1021/ja0713375,10.1002/anie.200702439,10.1055/s-2006-926232,10.1055/s-2003-370283/9/2022
267
302FALSEjacs.1c1220310.1021/jacs.1c12203https://sci-hub.wf/10.1021/jacs.1c12203https://doi.org/10.1021/jacs.1c12203NiC-O ActivationxWilliam12-JunTRUE171452022Doyle, AG
Ni/Chiral Sodium Carboxylate Dual Catalyzed Asymmetric O-Propargylation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
A highly enantioselective O-propargylation catalyzed by combining a phosphine-nickel complex and an axially chiral sodium dicarboxylate has been developed. The transformation features mild reaction conditions, a broad substrate scope, and excellent functional group tolerance, offering an efficient approach to an array of enantioenriched O-propargyl hydroxylamines. Mechanistic studies support the presumed role of the chiral carboxylate as a counterion for nickel catalysis enabling the discovery of highly stereoselective transformations. The power of this reaction is illustrated by its application in the asymmetric total synthesis of potent firefly luciferase inhibitors and (S)-dihydroyashabushiketol.
1/19/2022Csp3-Csp3E-EOX
(dimethoxymethyl)benzene
ClAlkylAlkylK3PO4Ionic-PO46/21/2022
268
310FALSEjacs.2c0206210.1021/jacs.2c02062https://sci-hub.wf/10.1021/jacs.2c02062https://doi.org/10.1021/jacs.2c02062NiC-O ActivationxWilliam4-JulyTRUE81#N/A2022
MacMillan, DWC
Using Data Science To Guide Aryl Bromide Substrate Scope Analysis in a Ni/Photoredox-Catalyzed Cross-Coupling with Acetals as Alcohol-Derived Radical Sources
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Ni/photoredox catalysis has emerged as a powerful platform for C(sp(2))-C(sp(3)) bond formation. While many of these methods typically employ aryl bromides as the C(sp(2)) coupling partner, a variety of aliphatic radical sources have been investigated. In principle, these reactions enable access to the same product scaffolds, but it can be hard to discern which method to employ because nonstandardized sets of aryl bromides are used in scope evaluation. Herein, we report a Ni/photoredox-catalyzed (deutero)methylation and alkylation of aryl halides where benzaldehyde di(alkyl) acetals serve as alcohol-derived radical sources. Reaction development, mechanistic studies, and late-stage derivatization of a biologically relevant aryl chloride, fenolibrate, are presented. Then, we describe the integration of data science techniques, including DFT featurization, dimensionality reduction, and hierarchical clustering, to delineate a diverse and succinct collection of aryl bromides that is representative of the chemical space of the substrate class. By superimposing scope examples from published Ni/photoredox methods on this same chemical space, we identify areas of sparse coverage and high versus low average yields, enabling comparisons between prior art and this new method. Additionally, we demonstrate that the systematically selected scope of aryl bromides can be used to quantify population-wide reactivity trends and reveal sources of possible functional group incompatibility with supervised machine learning.
Csp3-Csp3E-EOCsp2OHCOOHAlkylAlkylNo baseNo BaseStrong-0.817/6/2022
269
64FALSEjacs.5b0100510.1021/jacs.5b01005https://sci-hub.wf/10.1021/jacs.5b01005https://doi.org/10.1021/jacs.5b01005NiC-O ActivationGerryTRUE3811012015
Yamamoto, H
Nontraditional Fragment Couplings of Alcohols and Carboxylic Acids: C(sp(3))-C(sp(3)) Cross-Coupling via Radical Sorting
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Alcohols and carboxylic acids are among the most commercially abundant, synthetically versatile, and operationallyconvenient functional groups in organic chemistry. Under visible light photoredox catalysis, these native synthetic handles readilyundergo radical activation, and the resulting open-shell intermediates can subsequently participate in transition metal catalysis. Inthis report, we describe the C(sp3)-C(sp3) cross-coupling of alcohols and carboxylic acids through the dual combination ofN-heterocyclic carbene (NHC)-mediated deoxygenation and hypervalent iodine-mediated decarboxylation. This mild and practical Ni-catalyzed radical-coupling protocol was employed to prepare a wide array of alkyl-alkyl cross-coupled products, including highlycongested quaternary carbon centers from the corresponding tertiary alcohols or tertiary carboxylic acids. We demonstrate thesynthetic applications of this methodology to alcoholC1-alkylation and formal homologation, as well as to the late-stagefunctionalization of drugs, natural products, and biomolecules.
Univ Chicago4/8/2015Csp3-Nsp3E-NuOH
O(Ring-Opening)
HAlkyl
N(H)Aryl
No baseNo BaseWeak1_10.1021/acs.orglett.6b0223610.1016/j.tet.2021.132539,10.1021/acs.orglett.1c02412,10.1021/acscatal.1c00571,10.1002/chem.202004455,10.1021/acs.joc.0c01691,10.1039/d0ob00811g,10.1021/acscatal.9b04823,10.1002/adsc.201901268,10.1002/adsc.201901009,10.1155/2019/2381208,10.1039/c8ob02448k,10.1039/c8ob02141d,10.1039/c8sc04996c,10.1016/j.molstruc.2018.09.034,10.1039/c8cc07200k,10.1021/acscatal.8b02591,10.1021/acs.orglett.8b02295,10.1007/s13738-018-1400-5,10.1021/acs.joc.7b03180,10.1021/acs.chemrev.7b00514,10.1039/c7ob02318a,10.1021/acs.joc.7b02560,10.1055/s-0036-1589045,10.1021/acs.orglett.7b02076,10.1055/s-0036-1588356,10.1248/cpb.c16-00568,10.1246/cl.160783,10.1021/jacs.6b09482,10.1021/acscatal.6b01869,10.1002/bkcs.10871,10.1021/acs.joc.6b00050,10.1021/acs.accounts.5b00428,10.1016/bs.aihch.2016.04.002,10.1080/00397911.2016.1170148,10.1002/anie.2015033911/25/2022
270
175FALSEjacs.5b0190910.1021/jacs.5b01909https://sci-hub.wf/10.1021/jacs.5b01909https://doi.org/10.1021/jacs.5b01909NiC-O ActivationGerryTRUE1079382015Weix, DJ
Nickel-Catalyzed Regio- and Enantioselective Aminolysis of 3,4-Epoxy Alcohols
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
The first catalytic regio- and enantioselective aminolysis of 3,4-epoxy alcohols has been accomplished. Under the catalysis of Ni(ClO4)(2)center dot 6H(2)O, the C-4 selective ring opening of various 3,4-epoxy alcohols proceeded in a stereospecific manner with high regioselectivities. Furthermore, with the Ni-BINAM catalytic system the enantioselective ring opening of 3,4-epoxy alcohols furnished various gamma-hydroxy-delta-amino alcohols as products with complete regiocontrol and high enantioselectivities (up to 94% ee).
Univ Rochester3/11/2015Csp3-Csp2_arE-EOX
O(Ring-Opening)
XAlkylArylNitrogenNitrogen(neutral)Weak1_10.1039/c7sc03140h,10.1021/acs.orglett.8b03367,10.1002/chem.201601320,10.1039/c9cc08079a,10.1002/anie.201503936,10.1021/jacs.7b13601,10.1021/jacs.7b03448,10.1021/jacs.0c13093,10.1021/jacs.9b0386310.1021/acs.orglett.2c00217,10.1002/cjoc.202100819,10.1021/acs.oprd.1c00410,10.1055/s-0041-1737762,10.1021/acs.oprd.1c00410,10.1021/jacs.1c11170,10.1021/acs.orglett.1c03384,10.1038/s41467-021-26794-8,10.6023/cjoc202106021,10.1021/acscatal.1c04143,10.1021/jacs.1c08105,10.1021/jacs.1c08695,10.1021/jacs.1c05670,10.1039/c9cs00571d,10.1021/jacs.1c03827,10.1021/jacs.1c00659,10.1002/anie.202102769,10.1002/anie.202101076,10.1021/jacs.0c13093,10.1002/chem.202004437,10.1021/acs.joc.0c01233,10.1021/acs.chemrev.0c00245,10.1055/s-0040-1707216,10.1021/acscatal.0c03237,10.1002/adsc.202000945,10.1038/s41557-020-00561-6,10.1039/d0sc03217d,10.1002/anie.202007668,10.1002/ejoc.202000966,10.1021/acscatal.0c01842,10.1021/jacs.0c03708,10.1039/d0ob00535e,10.1021/acscatal.0c01199,10.1002/ejoc.201901853,10.1021/acs.orglett.0c00960,10.1038/s41929-020-0439-8,10.1002/anie.201914175,10.1039/c9cc08079a,10.1002/anie.201903726,10.1002/chem.201905048,10.1016/j.trechm.2019.08.004,10.1021/acs.joc.9b02465,10.1021/acs.orglett.9b03102,10.1039/c9cc04795f,10.1021/acs.orglett.9b01987,10.1021/jacs.9b04993,10.1021/jacs.9b03863,10.1021/acs.organomet.8b00720,10.1021/acs.orglett.8b03367,10.1021/acscatal.8b03930,10.1021/jacs.8b08605,10.1021/jacs.8b06458,10.1246/cl.180385,10.1021/acscatal.8b00244,10.1021/jacs.7b13710,10.1002/cjoc.201700745,10.1021/jacs.7b13601,10.1021/acs.orglett.8b00114,10.1021/acs.macromol.7b02042,10.1039/c7np00065k,10.1055/s-0036-1591853,10.1021/acs.accounts.7b00432,10.1039/c7sc03140h,10.1039/c8ra09048c,10.1055/s-0036-1589102,10.1021/jacs.7b06723,10.1038/s41570-017-0065,10.1002/cjoc.201700071,10.1021/acs.orglett.7b02076,10.1002/chem.201603124,10.1021/jacs.7b03448,10.1039/c6sc05556g,10.1039/c6cc07924e,10.1021/acs.orglett.6b02862,10.1021/jacs.6b08856,10.1021/jacs.6b08507,10.1021/acs.orglett.6b01675,10.1007/s41061-016-0042-2,10.1021/jacs.6b03384,10.1002/chem.201601320,10.1021/jacs.6b01533,10.1002/anie.201505090,10.1039/c6dt02185a,10.1039/c5cc09817c,10.1021/jacs.5b09223,10.1021/jacs.5b06255,10.1002/anie.201503936,10.1021/jacs.5b03870,10.1021/acs.accounts.5b00057,10.1039/c5qo00224aKelly1/19/2022
271
196FALSEjacs.6b0325310.1021/jacs.6b03253https://sci-hub.wf/10.1021/jacs.6b03253https://doi.org/10.1021/jacs.6b03253NiC-O ActivationKellyTRUE11213892016Chatani, N
Stereospecific Intramolecular Reductive Cross-Electrophile Coupling Reactions for Cyclopropane Synthesis
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
The stereospecific reductive cross-electrophile coupling reaction of 2-aryl-4-chlorotetrahydropyrans to afford disubstituted cyclopropanes is reported. This ring contraction presents surprises with respect to the stereochemical outcome of reaction of the alkyl halide moiety. While cross-coupling and reductive cross-electrophile coupling reactions of alkyl halides are typically stereoablative, using a chiral catalyst to set the stereocenter, this transformation proceeds with high stereochemical fidelity at the alkyl halide and ether bearing stereogenic centers. This approach provides straightforward access to highly substituted cyclopropanes in two steps from commercially available aldehydes.
Osaka Univ6/1/2016TRUETRUEFALSECsp2_ar-Csp3E-NuOHOMeHArylAlkylNo baseNo BaseStrong-0.28_xx10.1002/anie.201607646,10.1021/acscatal.8b03436,10.1039/c8sc00609a,10.1021/jacs.7b02326,10.1021/jacs.7b04279,10.1021/acscatal.7b01058,10.1021/jacs.8b02134,10.1002/ejic.201900692,10.1002/anie.201806790,10.1021/acscatal.1c04800,10.1021/jacs.1c09797,10.1039/c6cc09685a,10.1021/jacs.7b1286510.1021/acs.organomet.1c00578,10.1021/acscatal.1c04800,10.1021/jacs.1c09797,10.1002/adsc.202100585,10.1039/d1qo00811k,10.1039/d1sc02210e,10.1039/d1qo00549a,10.1021/acs.orglett.1c01053,10.1021/acscatal.1c01077,10.1021/jacs.1c03038,10.1126/science.abg5526,10.1055/a-1467-2494,10.6023/cjoc202006077,10.1021/acs.joc.0c02389,10.1246/cl.200750,10.1055/s-0040-1705986,10.1021/acs.orglett.0c03507,10.1002/chem.202004132,10.1016/j.tet.2020.131493,10.1021/acs.chemrev.0c00088,10.1002/asia.202000763,10.1021/acs.orglett.0c02609,10.1021/acs.orglett.0c02236,10.1021/acs.chemrev.9b00682,10.1021/acs.joc.0c00640,10.1002/cjoc.201900506,10.1246/cl.200083,10.1021/jacs.0c00283,10.1021/jacs.0c02839,10.1021/acscatal.0c00980,10.1055/s-0039-1690718,10.1016/j.trechm.2019.08.004,10.1021/acs.joc.9b01851,10.1021/acs.orglett.9b03170,10.1021/acscatal.9b02636,10.1246/cl.190393,10.1021/acs.oprd.9b00235,10.1002/cjoc.201800554,10.1002/ejic.201900692,10.1002/cctc.201900230,10.1002/cjoc.201800575,10.1021/acs.orglett.9b00946,10.1039/c8ob02977f,10.1021/acs.organomet.8b00720,10.1021/jacs.8b12063,10.1007/3418_2018_19,10.1039/c8cc08504h,10.1038/s42004-018-0092-1,10.1021/acscatal.8b03436,10.1002/anie.201809003,10.1021/acs.joc.8b02104,10.1021/acs.organomet.8b00438,10.1039/c8cc03665a,10.1002/anie.201806237,10.1002/anie.201806790,10.1021/acs.orglett.8b01696,10.1021/jacs.8b03669,10.1021/jacs.8b06228,10.1039/c8sc00609a,10.1021/acscatal.8b00856,10.1021/acscatal.8b01224,10.1038/s41467-018-03928-z,10.1021/acs.orglett.8b00313,10.1021/acs.orglett.8b00674,10.1021/jacs.8b02134,10.1021/jacs.7b12865,10.1039/c7cc08709h,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.1039/c7cc08416a,10.1002/chem.201703266,10.1055/s-0036-1588568,10.1021/acscatal.7b03465,10.1021/acscatal.7b03432,10.1055/s-0036-1589101,10.1021/jacs.7b08579,10.1002/anie.201707309,10.1248/cpb.c17-00487,10.1021/jacs.7b04279,10.1021/acscatal.7b01058,10.1021/jacs.7b02326,10.1002/ejoc.201700514,10.1039/c7cc00078b,10.1021/acs.organomet.7b00165,10.1002/adsc.201601105,10.1021/acs.orglett.6b03861,10.1021/acs.joc.7b00209,10.1246/bcsj.20160391,10.1021/acscatal.6b03543,10.1021/jacs.6b10998,10.1039/c6cc09685a,10.1021/acscatal.6b02964,10.1039/c6dt03241a,10.1002/anie.201607646,10.1002/ajoc.201600411,10.1021/jacs.6b10255,10.1246/cl.160712,10.1021/acs.organomet.6b00638,10.1002/asia.201600972,10.1002/adsc.201600590,10.1016/bs.adomc.2016.07.001,10.1039/c6cc05400eKelly11/10/2021JUN 12016FALSEFALSEFALSEFALSE138216711
272
288FALSEanie.20151074310.1002/anie.201510743https://sci-hub.wf/10.1002/anie.201510743https://doi.org/10.1002/anie.201510743NiC-H ActivationGerry8-FebTRUE96932016
Ackermann, L
A General Strategy for the Nickel-Catalyzed C-H Alkylation of Anilines
ANGEW CHEM INT EDIT
The C-H alkylation of aniline derivatives with both primary and secondary alkyl halides was achieved with a versatile nickel catalyst of a vicinal diamine ligand. Step-economic access to functionalized 2-pyrimidyl anilines, key structural motifs in anticancer drugs, is thus provided. The C-H functionalization proceeded through facile C-H activation and SET-type C-X bond cleavage with the assistance of a monodentate directing group, which could be removed in a traceless fashion.
Univ Gottingen2/24/2016TRUEFALSEFALSEyCsp2_ar-Csp3E-NuXHBrHArylAlkylLiOtBuIonic-OtBu_x10.1039/c6qo00149a,10.1021/acscatal.6b02003,10.1021/acscatal.7b01044,10.1002/ajoc.201700569,10.1002/anie.201709087,10.1021/acs.organomet.6b00201,10.1039/c9sc01446b,10.1021/acs.orglett.6b02236,10.1021/acscatal.6b0112010.1002/anie.202109953,10.1134/S0036023621100156,10.1055/a-1581-0934,10.1039/d1sc02937a,10.1002/chem.202101004,10.1039/d1qo00727k,10.1039/d1sc01731d,10.1021/acs.joc.1c00500,10.1021/acscatal.1c00714,10.1016/j.tetlet.2021.152872,10.1021/jacs.1c00237,10.1021/acscatal.0c05580,10.1016/bs.adomc.2021.04.003,10.1021/acs.orglett.0c02609,10.1016/j.chempr.2020.04.006,10.1002/anie.202004958,10.1021/acs.orglett.0c01126,10.1002/cjoc.201900468,10.3390/molecules25051141,10.1039/c9dt04470a,10.1021/acs.joc.9b02954,10.1021/acs.accounts.9b00510,10.1039/c9sc01446b,10.1002/anie.201906658,10.1016/j.tet.2019.05.047,10.1016/j.trechm.2019.06.002,10.1039/c9ra03421h,10.1021/acs.orglett.9b01641,10.1021/acs.orglett.9b01846,10.1039/c9sc00554d,10.1002/anie.201806629,10.1021/acs.organomet.9b00113,10.1039/c9qo00066f,10.1039/c9cy00009g,10.1021/acs.organomet.8b00899,10.1038/s42004-019-0132-5,10.1039/c8qo01274a,10.1021/acs.chemrev.8b00507,10.1002/anie.201813191,10.1021/acs.orglett.8b03924,10.1002/chem.201805441,10.1039/c8cy01860j,10.1021/acscatal.8b03770,10.1021/acs.joc.8b02197,10.1021/acs.orglett.8b02736,10.1039/c8cs00201k,10.1039/c8cc04233k,10.1021/acs.orglett.8b01395,10.1055/s-0037-1610142,10.1021/acs.joc.8b00714,10.1021/acs.organomet.8b00025,10.1039/c8ob00147b,10.1016/j.chempr.2017.11.002,10.1039/c7sc04604a,10.1002/anie.201710520,10.1002/ajoc.201700569,10.1002/anie.201709087,10.1002/anie.201708961,10.1039/c7ob01899a,10.1021/acs.orglett.7b02823,10.1002/anie.201706237,10.1039/c7cc05532c,10.1039/c7ob01791j,10.1002/chem.201703191,10.1039/c7cc05011a,10.1021/acs.orglett.7b01946,10.1039/c7sc01732d,10.1021/jacs.7b03548,10.1002/chem.201605657,10.1021/acscatal.7b01044,10.1002/cssc.201700321,10.1039/c6sc05622a,10.1039/c7cc01201b,10.1021/acs.orglett.7b00479,10.1002/adsc.201601105,10.1021/acscatal.6b03236,10.1002/chem.201605306,10.1021/acs.organomet.6b00810,10.1016/bs.adomc.2017.04.003,10.1002/chem.201604621,10.1007/s40010-016-0289-6,10.1021/acscatal.6b02477,10.1002/chem.201603848,10.1002/anie.201606529,10.1021/acs.orglett.6b02236,10.1002/chem.201603092,10.1021/acscatal.6b02003,10.1002/anie.201603260,10.1021/acs.inorgchem.6b01162,10.1007/s41061-016-0053-z,10.1002/adsc.201600384,10.1021/acscatal.6b01120,10.1021/acs.organomet.6b00201,10.1039/c6qo00149a11/22/2021FEB 242016FALSEFALSEFALSEFALSE5593153
273
158FALSEjacs.6b0807510.1021/jacs.6b08075https://sci-hub.wf/10.1021/jacs.6b08075https://doi.org/10.1021/jacs.6b08075NiC-O ActivationShihongTRUE888272016Watson, MP
Nickel-Catalyzed Alkylative Cross-Coupling of Anisoles with Grignard Reagents via C-O Bond Activation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
We report nickel-catalyzed cross-coupling of methoxyarenes with alkylmagnesium halides, in which a methoxy group is eliminated. A wide range of alkyl groups, including those bearing beta-hydrogens, can be introduced directly at the ipso position of anisole derivatives. We demonstrate that the robustness of a methoxy group allows this alkylation protocol to be used to synthesize elaborate molecules by combining it with traditional cross coupling reactions or oxidative transformation. The success of this method is dependent on the use of alkylmagnesium iodides, but not chlorides or bromides, which highlights the importance of the halide used in developing catalytic reactions using Grignard reagents.
Univ Delaware9/21/2016TRUETRUEFALSECsp3-Csp2_arE-NuOBOAcB(nep)AlkylArylNaOMeIonic-ORMedium0.31_xx10.1002/anie.201814524,10.1021/jacs.7b04973,10.1021/jacs.8b02134,10.1126/science.abj4213,10.1021/jacs.1c03898,10.1021/jacs.9b00097,10.1055/s-0036-1588845,10.1039/c8sc00609a10.1039/d1sc05605k,10.1021/acs.orglett.1c03963,10.1021/acscatal.1c05530,10.1021/acs.orglett.1c03963,10.6023/cjoc202106021,10.1126/science.abj4213,10.1002/tcr.202100210,10.1021/jacs.1c03898,10.1039/d1sc01217g,10.1021/acs.organomet.1c00085,10.1055/s-0040-1720406,10.1016/j.tetlet.2021.152947,10.1039/d0cs01107j,10.1002/anie.202014080,10.1021/acs.orglett.0c04316,10.1002/anie.202015021,10.1021/acscatal.0c05484,10.2174/1570179418666210224124931,10.1038/s41467-020-18658-4,10.1021/acs.orglett.0c01284,10.1021/jacs.0c02237,10.1021/jacs.0c02355,10.1016/j.tetlet.2020.151729,10.1039/c9cc09899b,10.1002/anie.201914315,10.1016/j.trechm.2019.08.004,10.1021/acs.orglett.9b03475,10.1021/acscatal.9b02636,10.1039/c9cc05385a,10.1002/anie.201909852,10.1021/acs.orglett.9b01669,10.1021/jacs.9b03991,10.1021/jacs.9b00097,10.1039/c8qo01258j,10.1038/s41467-019-09249-z,10.1002/anie.201814524,10.1021/jacs.8b11868,10.1039/c8cc07781a,10.1002/adsc.201801000,10.1002/adsc.201801135,10.1039/c8cc07093h,10.1016/j.tet.2018.09.036,10.1038/s41467-018-07069-1,10.1021/jacs.8b09473,10.1021/acs.joc.8b01763,10.1039/c8ob01389f,10.1021/acs.orglett.8b02196,10.1039/c8qo00632f,10.1039/c8qo00517f,10.1021/acs.organomet.8b00244,10.1021/acscatal.8b01572,10.1055/s-0037-1609575,10.1002/anie.201804479,10.1039/c8cc03541e,10.1039/c8cc02380h,10.1016/j.jorganchem.2018.01.019,10.1039/c8sc00609a,10.1002/anie.201800829,10.1021/acs.orglett.8b00413,10.1021/jacs.8b02134,10.1021/acs.orglett.8b00105,10.1021/acs.accounts.7b00432,10.1021/jacs.7b10855,10.1021/acscatal.7b03388,10.1002/anie.201709411,10.1055/s-0036-1588563,10.1055/s-0036-1590962,10.1021/jacs.7b04973,10.1002/anie.201706631,10.1021/acs.orglett.7b02063,10.1055/s-0036-1588845,10.1021/jacs.7b04374,10.1021/acs.orglett.7b01135,10.1021/jacs.7b03781,10.1021/jacs.7b03371,10.1021/jacs.7b01254,10.1021/acscatal.7b00300,10.1021/acscatal.6b03434,10.1002/anie.201609844,10.1021/acscentsci.6b00283,10.1021/jacs.6b09533Kelly11/5/2021SEP 212016FALSEFALSEFALSEFALSE1383712057
274
290FALSEc7sc01980g10.1039/c7sc01980ghttps://sci-hub.wf/10.1039/c7sc01980ghttps://doi.org/10.1039/c7sc01980gNiC-N ActivationLongTRUE1012542017Garg, NK
Nickel-catalyzed transamidation of aliphatic amide derivativesCHEM SCI
Transamidation, or the conversion of one amide to another, is a long-standing challenge in organic synthesis. Although notable progress has been made in the transamidation of primary amides, the transamidation of secondary amides has remained underdeveloped, especially when considering aliphatic substrates. Herein, we report a two-step approach to achieve the transamidation of secondary aliphatic amides, which relies on non-precious metal catalysis. The method involves initial Boc-functionalization of secondary amide substrates to weaken the amide C-N bond. Subsequent treatment with a nickel catalyst, in the presence of an appropriate amine coupling partner, then delivers the net transamidated products. The transformation proceeds in synthetically useful yields across a range of substrates. A series of competition experiments delineate selectivity patterns that should influence future synthetic design. Moreover, the transamidation of Boc-activated secondary amide derivatives bearing epimerizable stereocenters underscores the mildness and synthetic utility of this methodology. This study provides the most general solution to the classic problem of secondary amide transamidation reported to date.
Univ Calif Los Angeles
9/1/2017TRUETRUEFALSECsp2-Nsp3E-NuNH
N(Bn)Boc
H
Carbonyl
N(H)Alkyl
NaOtBuIonic-OtBu_x10.1021/acscatal.7b03688,10.1021/acs.orglett.8b0102110.1021/acscatal.1c05738,10.1039/d1ob02414k,10.1039/d1ob02349g,10.1021/acs.joc.1c02245,10.1021/acs.joc.1c02245,10.1021/acs.joc.1c02077,10.1002/ejoc.202101114,10.1016/j.tetlet.2021.153457,10.1021/acssuschemeng.1c05307,10.1080/00397911.2021.1989597,10.1002/tcr.202100224,10.1039/d1ob01409a,10.1039/d1ob01021b,10.1002/bkcs.12371,10.1021/acs.orglett.1c01622,10.1039/d1cc01701b,10.1021/acscatal.1c01840,10.1055/a-1517-5895,10.6023/cjoc202009048,10.1002/chem.202100093,10.1021/acs.orglett.0c04300,10.1021/acssuschemeng.0c08262,10.1021/acs.joc.0c02843,10.3390/molecules26010188,10.1016/j.jorganchem.2020.121555,10.1039/d0sc05137c,10.1039/d0cc04960c,10.1002/adsc.202000794,10.1021/acscatal.0c03334,10.1039/d0qo00797h,10.1016/j.trechm.2020.08.001,10.1039/d0qo00713g,10.1055/s-0040-1707101,10.1246/bcsj.20200116,10.1021/acs.orglett.0c00958,10.1021/acscatal.9b05074,10.1021/acs.orglett.0c00885,10.1021/acs.orglett.0c00485,10.1038/s41467-020-14799-8,10.1039/c9cy02080b,10.1021/acs.orglett.9b03434,10.1002/tcr.201900072,10.1039/c9ob02096a,10.1055/s-0039-1690178,10.1177/1747519819873514,10.1002/adsc.201900819,10.1039/c9cc05763c,10.1021/acs.joc.9b01699,10.1021/acs.joc.9b02013,10.1021/acs.orglett.9b02862,10.1021/acs.joc.9b01103,10.1021/acs.orglett.9b02306,10.1002/ajoc.201900216,10.1002/anie.201803797,10.1002/adsc.201900485,10.1002/ajoc.201900317,10.1016/j.tet.2019.05.027,10.1039/c9nj01748h,10.1039/c9qo00106a,10.1002/ejoc.201900517,10.1002/ajoc.201900128,10.1021/acs.jchemed.8b00489,10.3390/molecules24071234,10.1021/acs.orglett.9b00554,10.1002/chem.201802635,10.1039/c8qo01052h,10.1055/s-0037-1610664,10.1002/asia.201801560,10.1039/c8ob03010c,10.1021/acs.orglett.8b03542,10.1021/acs.organomet.8b00720,10.1039/c8cc08693a,10.1002/asia.201801317,10.1021/acs.orglett.8b03304,10.1039/c8ob01832d,10.1039/c8cs00335a,10.1039/c8qo00591e,10.1038/s41467-018-06623-1,10.3390/molecules23102681,10.1021/acs.orglett.8b02303,10.1021/acs.orglett.8b01896,10.1021/acs.oprd.8b00182,10.1002/ajoc.201800258,10.1021/acs.orglett.8b01654,10.1002/ejoc.201800109,10.1021/jacs.8b03739,10.1039/c8qo00184g,10.1021/acs.orglett.8b01021,10.1021/acs.orglett.8b00949,10.1021/acs.joc.8b00174,10.1039/c7ob02874a,10.1021/acscatal.7b03688,10.1055/s-0036-1590932,10.1021/acscatal.7b02599,10.1021/acs.orglett.7b03191,10.1039/c7ob02269g,10.1021/jacs.7b09482,10.1021/acscatal.7b0285911/1/2021SEP 12017FALSEFALSEFALSEFALSE896433
275
177FALSEjacs.6b1141210.1021/jacs.6b11412https://sci-hub.wf/10.1021/jacs.6b11412https://doi.org/10.1021/jacs.6b11412NiC-O ActivationShihongTRUE988462017Hazari, N
Stereospecific Cross Couplings To Set Benzylic, All-Carbon Quaternary Stereocenters in High Enantiopurity
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Asymmetric preparation of all-carbon quaternary stereocenters is an important goal. Despite advances in formation of highly enantioenriched products with quaternary stereocenters proximal to a functional group, methods to install quaternary stereocenters isolated from functional groups are limited. Transition metal catalysis offers a potential solution, but prior cross couplings are limited to allylic substrates or deliver little to no enantiomeric enrichment. We report a stereospecific, nickel-catalyzed Suzuki-Miyaura arylation of tertiary benzylic acetates to deliver products with diaryl and triaryl quaternary stereocenters in high-yield's and ee's. This reaction employs an inexpensive, air-stable Ni(II) salt and commercially available phosphine ligand to transform tertiary alcohol derivatives, which are easily available in exceptional ee, into valuable products with stereoretention.
Yale Univ1/18/2017TRUETRUEFALSECsp2_ar-Csp2_arE-NuOB
OSO2NMe2
B(OH)2ArylArylK3PO4Ionic-PO4Weak0.36_10.1021/acscatal.8b01879,10.1002/anie.202006826,10.1021/jacs.7b04973,10.1021/acscatal.9b00744,10.1038/s41929-020-00560-3,10.1021/jacs.7b04312,10.1021/jacs.0c06995,10.1021/acscatal.1c0480010.1039/d1sc05605k,10.1021/acscatal.1c05386,10.1021/acscatal.1c05386,10.1007/s40843-021-1910-2,10.1021/acscatal.1c04800,10.1002/anie.202112251,10.1039/d1qo01153g,10.1021/acs.inorgchem.1c02397,10.3390/molecules26216703,10.1016/j.xcrp.2021.100574,10.1021/jacs.1c05274,10.1002/chem.202101880,10.1055/a-1548-8362,10.1002/anie.202102481,10.1021/acs.organomet.1c00033,10.1039/d1cy00374g,10.1039/d1cc00203a,10.1038/s41929-020-00560-3,10.1039/d0ra09639c,10.1021/acscatal.0c04956,10.1016/j.tetlet.2020.152605,10.1021/acscatal.0c03237,10.1021/acscatal.0c03334,10.1021/acsomega.0c03415,10.1021/acscatal.0c02514,10.1021/jacs.0c06995,10.1002/cctc.202000876,10.1002/anie.202006826,10.1039/d0cc02542a,10.1021/acs.inorgchem.0c01115,10.1039/d0sc01813a,10.2533/chimia.2020.495,10.1021/jacs.0c03708,10.1021/acs.organomet.9b00834,10.1016/j.ica.2020.119457,10.1021/acs.organomet.0c00060,10.1021/acs.accounts.0c00032,10.1021/acsomega.9b04450,10.3390/catal10040372,10.1016/j.chempr.2019.12.010,10.1039/c9sc05444h,10.1002/chem.202000215,10.1002/ijch.201900139,10.1021/acs.organomet.9b00672,10.1016/j.trechm.2019.08.004,10.1021/jacs.9b10771,10.1016/j.jorganchem.2019.120937,10.1039/c9cy01365b,10.1021/jacs.9b10026,10.1002/anie.201906815,10.1021/acs.organomet.9b00543,10.1039/c9cy00752k,10.1021/acs.orglett.9b02797,10.1021/acs.jpca.9b04284,10.1039/c9ob00561g,10.1039/c9qo00066f,10.1021/acscatal.9b00566,10.1021/acscatal.9b00744,10.1021/jacs.9b00939,10.1002/anie.201814233,10.1021/acs.inorgchem.8b03389,10.1021/acs.chemrev.8b00361,10.1021/jacs.8b13499,10.1039/c8nj05503c,10.1021/acs.organomet.8b00720,10.1016/j.jcou.2018.12.007,10.1039/c8dt03188f,10.1016/j.tet.2018.10.025,10.1021/acs.organomet.8b00589,10.1021/acs.orglett.8b02264,10.1016/j.jcat.2018.07.007,10.1021/acscatal.8b01879,10.1021/acscatal.8b00933,10.1016/j.jorganchem.2018.01.019,10.1021/acscatal.8b00856,10.1002/cctc.201701709,10.1021/acscatal.8b00230,10.1021/acscatal.8b00546,10.1039/c7ob02531a,10.1016/j.mcat.2017.10.004,10.1021/acs.organomet.7b00651,10.1002/chem.201702331,10.1002/anie.201706423,10.1039/c7dt02532g,10.1021/acs.organomet.7b00642,10.1021/acs.organomet.7b00446,10.1021/jacs.7b04973,10.1039/c7cs00216e,10.1002/adsc.201700672,10.1021/jacs.7b04312,10.1021/acs.organomet.7b00129,10.1021/acs.organomet.7b00208,10.1038/s41570-017-0025 Long 11/5/2021JAN 182017FALSEFALSEFALSEFALSE1392922
276
292FALSEjacs.7b0619110.1021/jacs.7b06191https://sci-hub.wf/10.1021/jacs.7b06191https://doi.org/10.1021/jacs.7b06191NiC-N ActivationLongTRUE718#N/A2017Stanley, LM
Ni-Catalyzed Alkene Carboacylation via Amide C-N Bond Activation
J AM CHEM SOC
We report Ni-catalyzed formal carboacylation of o-allylbenzamides with arylboronic acid pinacol esters. The reaction is triggered by oxidative addition of an activated amide C-N bond to a Ni(0) catalyst and proceeds via alkene insertion into a Ni(II)-acyl bond. The exo-selective carboacylation reaction generates 2-benzy-12,3-dihydro-1H-inden-1-ones in moderate to high yields (46-99%) from a variety of arylboronic acid pinacol esters and substituted o-allylbenzamides. These results show that amides are practical substrates for alkene carboacylation via amide C-N bond activation) and this approach bypasses challenges associated with alkene carboacylation triggered by C-C bond activation.
Iowa State Univ8/2/2017TRUEFALSEFALSECsp2-Csp2_arE-NuNB
N(Bn)Boc
Bpin
Carbonyl
ArylK3PO4Ionic-PO4_x10.1021/acscatal.9b00884,10.1002/anie.202103327,10.1021/jacs.9b00111,10.1002/anie.201808560,10.1021/acscatal.0c00246,10.1021/acs.orglett.8b01021,10.1021/jacs.9b03863,10.1021/acs.orglett.9b0024210.1021/acs.orglett.1c03739,10.1021/acs.orglett.1c02093,10.1021/acscatal.1c02277,10.1002/anie.202103327,10.1002/adsc.202100293,10.1002/chem.202100390,10.1021/acs.joc.1c00087,10.1021/acs.orglett.1c00940,10.1039/d0nj06318e,10.1021/acs.orglett.1c00464,10.1021/acs.accounts.0c00771,10.1016/j.tetlet.2020.152801,10.1021/acscatal.0c05449,10.1021/acs.joc.0c02843,10.1021/acs.orglett.0c03897,10.1016/j.tet.2020.131724,10.1021/jacs.0c09949,10.1021/acs.orglett.0c03210,10.1039/d0cc04960c,10.1021/acscatal.0c03334,10.1039/d0qo00632g,10.1039/d0ob01083a,10.1039/d0sc02054k,10.1021/acscatal.0c02115,10.1021/acs.orglett.0c01607,10.1002/cjoc.202000224,10.1080/00397911.2020.1771370,10.1021/acscatal.0c01000,10.1021/jacs.0c02405,10.1021/acs.orglett.0c00688,10.1038/s42004-020-0292-3,10.1021/acscatal.0c00246,10.1021/jacs.9b12554,10.1021/acs.joc.9b02826,10.1002/anie.201913367,10.1039/c9cc07558e,10.1021/acs.orglett.9b03682,10.1021/acs.joc.9b02303,10.1021/acscatal.9b03574,10.1039/c9cc07710c,10.1039/c9sc03169c,10.1002/anie.201911372,10.1039/c9cc05763c,10.1021/acs.orglett.9b02933,10.1002/anie.201907840,10.1021/acs.oprd.9b00199,10.1002/ajoc.201900317,10.1039/c9nj01748h,10.1021/acscatal.9b01620,10.1016/j.tet.2019.03.047,10.1021/jacs.9b03863,10.1021/acs.orglett.9b01053,10.1021/acscatal.9b00884,10.1021/acs.jchemed.8b00489,10.1002/ajoc.201900119,10.1039/c8sc05819a,10.1021/acsomega.9b00081,10.1021/acs.orglett.8b03901,10.1002/chem.201802635,10.1021/acs.orglett.9b00242,10.1021/jacs.9b00111,10.1021/jacs.8b12495,10.1002/anie.201813182,10.1002/asia.201801317,10.1021/jacs.8b09401,10.1039/c8cs00335a,10.1021/acs.orglett.8b02911,10.1039/c8qo00591e,10.1021/jacs.8b08190,10.1021/acscatal.8b02815,10.3390/molecules23102681,10.1002/anie.201808560,10.1002/tcr.201700098,10.1038/s41467-018-06019-1,10.1038/s41467-018-05951-6,10.1021/jacs.8b05374,10.1002/cctc.201800511,10.1021/acs.orglett.8b01646,10.1021/jacs.8b03163,10.1002/adsc.201800100,10.1002/ejoc.201800109,10.1039/c8cc02636j,10.1021/acs.orglett.8b01021,10.1016/j.tetlet.2018.03.046,10.1021/acs.orglett.8b00949,10.1016/j.tetlet.2018.01.097,10.1021/acs.orglett.8b00086,10.1039/c7ob02874a,10.1039/c7sc04351a,10.1021/acscatal.7b02599,10.1021/acs.orglett.7b03191,10.1039/c7ob02269g,10.1021/jacs.7b09482,10.1021/acscatal.7b02540,10.1021/acs.orglett.7b0228810/31/2021AUG 22017FALSEFALSEFALSEFALSE1393010228
277
70FALSEjacs.7b0232610.1021/jacs.7b02326https://sci-hub.wf/10.1021/jacs.7b02326https://doi.org/10.1021/jacs.7b02326NiC-O ActivationGerryTRUE445282017Shi, ZJ
Mechanistic Study of an Improved Ni Precatalyst for Suzuki-Miyaura Reactions of Aryl Sulfamates: Understanding the Role of Ni(I) Species
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Nickel precatalysts are potentially a more sustainable alternative to traditional palladium precatalysts for the Suzuki-Miyaura coupling reaction. Currently, there is significant interest in Suzuki-Miyaura coupling reactions involving readily accessible phenolic derivatives such as aryl sulfamates, as the sulfamate moiety can act as a directing group for the prefunctionalization of the aromatic backbone of the electrophile prior to cross-coupling. By evaluating complexes in the Ni(0), (I), and (II) oxidation states we report a precatalyst, (dppf)Ni(o-tolyl) ( Cl) (dppf = 1,1'-bis(diphenylphosphino)-ferrocene), for Suzuki-Miyatra coupling reactions involving aryl sulfamates and boronic acids, which operates at a significantly lower catalyst loading and at milder reaction conditions than other reported systems. In some cases it can even function at room temperature. Mechanistic studies on precatalyst activation and the speciation of nickel during catalysis reveal that Ni(I) species,are formed in the catalytic reaction via two different pathways: (i) the precatalyst (dppf)Ni(o-tolyl)(Cl) undergoes, comproportionation with the active Ni(0). species; and (ii) the catalytic intermediate (dppf)Ni(Ar)(sulfamate) (Ar = aryl) undergoes comproportionation with the active Ni(0) species. In both cases the formation of Ni(I) is detrimental to Catalysis, which is proposed to proceed via a Ni(0)/Ni(II) cycle. DFT calculations are used to support experimental observations and provide insight about the elementary steps involved in reactions directly on the catalytic cycle, as well as off-cycle processes,. Our mechanistic investigation provides guidelines for designing even more active nickel catalysts.
Peking Univ5/17/2017yCsp3-ring(s)-Csp3-ring(s)E-EOOOPhOPhBenzylBenzylNo baseNo BaseStrong-0.32_x10.1039/c8sc00609a,10.1021/jacs.7b04973,10.1021/jacs.9b05224,10.1039/c9sc03347e,10.1021/jacs.8b0877910.1039/d2qo00043a,10.1002/hlca.202100184,10.1021/acscatal.1c04128,10.1002/anie.202107356,10.1021/acs.orglett.1c01879,10.1002/anie.202107490,10.1021/acs.orglett.1c02225,10.1002/ejoc.202100565,10.1038/d41586-021-01205-6,10.1038/s41586-021-03448-9,10.1055/a-1507-4153,10.1021/acs.accounts.1c00096,10.1055/a-1467-2432,10.1246/bcsj.20200277,10.1055/a-1349-3543,10.1021/acs.joc.0c01274,10.6023/cjoc202002038,10.1021/jacs.0c05730,10.1021/acs.chemrev.9b00682,10.1021/jacs.0c00283,10.1021/jacs.0c02839,10.1055/s-0039-1691525,10.1021/acs.jpcb.0c01123,10.1016/j.tetlet.2019.150955,10.1039/c9sc03347e,10.1021/acscatal.9b02636,10.1021/acs.orglett.9b02504,10.1021/jacs.9b05224,10.1039/c8gc02280a,10.1021/jacs.8b08779,10.1002/adsc.201800783,10.1021/jacs.8b08190,10.1016/j.jorganchem.2018.01.019,10.1039/c8sc00609a,10.1021/acscatal.8b01224,10.1055/s-0036-1591853,10.1055/s-0036-1588568,10.1039/c7ob02012k,10.1039/c7dt02498c,10.1021/jacs.7b049731/5/2022
278
108FALSEjacs.7b0427910.1021/jacs.7b04279https://sci-hub.wf/10.1021/jacs.7b04279https://doi.org/10.1021/jacs.7b04279NiC-O ActivationShihongTRUE595282017Mori, S
Deoxygenation of Ethers To Form Carbon-Carbon Bonds via Nickel Catalysis
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
In this article a successful protocol was developed to construct carbon carbon bonds by the extrusion of the O atom of ethers-via nickel catalysis in the presence of reductants. This methodology is featured as a highly economic route to construct sp(3)-sp(3) C-C bonds through dual C-O activation of ethers with good functional group tolerance.
Ibaraki Univ8/2/2017TRUEFALSEFALSECsp2_ar-Csp2_arE-NuOBOMeB(nep)ArylArylNaOtBuIonic-OtBuStrong-0.28_xx10.1021/acscatal.8b03436,10.1021/jacs.8b02134,10.1021/acscatal.1c04800,10.1002/anie.202004116,10.1021/jacs.9b0009710.1021/acs.joc.1c02737,10.1021/acs.joc.1c02737,10.1021/acscatal.1c04800,10.1007/s11244-021-01527-9,10.1002/anie.202110785,10.1021/acs.jpca.1c05412,10.1039/d1cc05408b,10.1021/acscatal.1c02790,10.1055/a-1509-5954,10.1039/d1qo00656h,10.1055/a-1507-6419,10.1021/jacs.1c03038,10.1021/acs.accounts.1c00050,10.1070/RCR4977,10.1039/d0cs01339k,10.1246/bcsj.20200277,10.1055/a-1349-3543,10.1021/acs.orglett.0c03507,10.1002/chem.202004132,10.1021/acs.chemrev.0c00088,10.1002/asia.202000763,10.1021/acs.orglett.0c02236,10.1021/jacs.0c05730,10.1002/anie.202004116,10.1021/acs.joc.0c00640,10.1021/jacs.0c00283,10.1021/acsomega.9b04450,10.1016/j.trechm.2019.08.004,10.1021/acs.joc.9b02154,10.1021/acs.orglett.9b03170,10.1021/acscatal.9b02636,10.1002/chem.201900498,10.1021/jacs.9b00097,10.3390/molecules24071234,10.1021/acs.organomet.8b00720,10.1002/anie.201809889,10.1007/3418_2018_19,10.1021/acscatal.8b03436,10.1039/c8dt03188f,10.1016/j.tet.2018.10.025,10.1021/acs.joc.8b02104,10.1021/acs.orglett.8b01696,10.1016/j.jorganchem.2018.01.019,10.1021/acscatal.8b01224,10.1038/s41467-018-03928-z,10.1021/acs.organomet.8b00046,10.1021/acs.orglett.8b00674,10.1021/jacs.8b02134,10.1002/ajoc.201700645,10.1002/cjoc.201700664,10.1070/RCR4795,10.1039/c7cc08416a,10.1055/s-0036-1590962,10.1039/c7dt02532gKelly11/5/2021AUG 22017FALSEFALSEFALSEFALSE1393010347
279
141FALSEjacs.7b0497310.1021/jacs.7b04973https://sci-hub.wf/10.1021/jacs.7b04973https://doi.org/10.1021/jacs.7b04973NiC-O ActivationLongTRUE745382017Hong, X
Combined Theoretical and Experimental Studies of Nickel-Catalyzed Cross-Coupling of Methoxyarenes with Arylboronic Esters via C-O Bond Cleavage
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Nickel(0)-catalyzed cross-coupling of methoxyarenes through C-O bond activation has been the subject of considerable research because of their favorable features compared with those of the cross-coupling of aryl halides, such as atom economy and efficiency. In 2008, we have reported nickel/PCy3-catalyzed cross-coupling of methoxyarenes with arylboronic esters in which the addition of a stoichiometric base such as CsF is essential for the reaction to proceed. Recently, we have also found that the scope of the substrate in the Suzuki Miyaura-type cross-coupling of methoxyarenes can be greatly expanded by using 1,3-dicyclohexylimidazol-2-ylidene (ICy) as the ligand. Interestingly, a stoichiometric amount of external base is not, required for the nickel/ICy-catalyzed cross-coupling. For the mechanism and origin elucidated, density functional theory calculations are conducted. In the nickel/PCy3-catalyzed reactions, the activation energy for the oxidative addition of the Caryl)-OMe bond is too high to occur under the catalytic conditions. However, the oxidative addition process becomes energetically feasible when CsF and an arylboronic ester interact with a Ni(PCy3)(2)/methoxyarene fragment to form a quaternary complex. In the nickel/ICy-catalyzed reactions, the oxidative addition of the Caryl)-OMe bond can proceed more easily without the aid of CsF because the nickel-ligand bonds are stronger and therefore stabilize the transition state. The subsequent transmetalation from an Ar-Ni-OMe intermediate is determined to proceed through a pathway with lower energies than those required for beta-hydrogen elimination. The overall driving force of the reaction is the reductive elimination to form the carbon carbon bond.
Zhejiang Univ9/20/2017TRUETRUETRUEyyCsp2_ar-Csp2_arE-NuOBOPivB(nep)ArylArylKOtBuIonic-OtBuMedium0.33_10.1021/jacs.8b02134,10.1038/s41929-020-00560-3,10.1021/jacs.1c03898,10.1021/jacs.1c08399,10.1021/jacs.9b0009710.1039/d1sc05605k,10.1021/acscatal.1c00247,10.1039/d1dt03353k,10.1039/d1qo01500a,10.1021/jacs.1c08399,10.6023/cjoc202106021,10.1021/acscatal.1c03980,10.1002/tcr.202100210,10.1021/acs.accounts.1c00075,10.1021/acs.organomet.1c00280,10.1021/jacs.1c03898,10.1021/acs.organomet.1c00085,10.1021/acs.accounts.1c00050,10.1039/d0qo01589j,10.1039/d0dt04121a,10.1016/j.cclet.2020.04.005,10.1038/s41929-020-00560-3,10.1021/acscatal.0c05484,10.1021/acscatal.0c04620,10.1039/d0sc04578k,10.1055/s-0040-1705987,10.1021/jacs.0c09639,10.1039/d0qo00903b,10.1021/acscatal.0c03334,10.1002/anie.202010840,10.1021/acs.joc.0c00597,10.1021/acs.orglett.0c00047,10.1002/chem.202000215,10.1002/adsc.201901398,10.1016/j.trechm.2019.08.004,10.1021/jacs.9b10771,10.1002/adsc.201901136,10.1021/acs.joc.9b02154,10.1039/c9cy01239g,10.1021/acscatal.9b02636,10.1021/acs.joc.9b01692,10.1002/anie.201907375,10.1021/acs.joc.9b01227,10.1021/acs.jpca.9b04284,10.1021/acs.inorgchem.9b01392,10.1021/acs.organomet.9b00082,10.1021/jacs.9b00097,10.1002/anie.201900659,10.1021/acs.chemrev.8b00361,10.1021/jacs.8b12568,10.1039/c8nj05503c,10.1002/ejoc.201801494,10.1021/acs.organomet.8b00723,10.1039/c8cc07093h,10.1002/qua.25723,10.1016/j.ica.2018.06.045,10.1002/adsc.201800729,10.1055/s-0037-1609575,10.1039/c8cc04456b,10.1021/acs.orglett.8b01323,10.1021/acscatal.8b00933,10.1016/j.jorganchem.2018.01.019,10.1016/j.jorganchem.2018.03.015,10.1021/jacs.8b02134,10.1021/acs.joc.7b03213,10.1002/ajoc.201700645,10.1021/acs.accounts.7b00432,10.1021/jacs.7b10855,10.1002/anie.201708748,10.1039/c7cc08416a Long 11/9/2021SEP 202017FALSEFALSEFALSEFALSE1393712994
280
153FALSEjacs.7b1170710.1021/jacs.7b11707https://sci-hub.wf/10.1021/jacs.7b11707https://doi.org/10.1021/jacs.7b11707NiC-O ActivationShihongTRUE974362018Reisman, SE
Mechanism and Origins of Ligand-Controlled Stereoselectivity of Ni-Catalyzed Suzuki-Miyaura Coupling with Benzylic Esters: A Computational Study
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Nickel catalysts have shown unique ligand control of stereoselectivity in the Suzuki-Miyaura cross-coupling of boronates with benzylic pivalates and derivatives involving C(sp(3))-O cleavage. The SIMes ligand (1,3-dimesity1-4,5-dihydroimidazol-2-ylidene) produces the stereochemically inverted C-C coupling product, while the tricyclohexylphosphine (PCy3) ligand delivers the retained stereochemistry. We have explored the mechanism and origins of the ligand-controlled stereoselectivity with density functional theory (DFT) calculations. The oxidative addition determines the stereoselectivity with two competing transition states, an S(N)2 back-side attack type transition state that inverts the benzylic stereogenic center and a concerted oxidative addition through a cyclic transition state, which provides stereoretention. The key difference between the two transition states is the substrate-nickel-ligand angle distortion; the ligand controls the selectivity by differentiating the ease of this angle distortion. For the PCy3 ligand, the nickel-ligand interaction involves mainly sigma-donation, which does not require a significant energy penalty for the angle distortion. The facile angle distortion with PCy3 ligand allows the favorable cyclic oxidative addition transition state, leading to the stereoretention. For the SIMes ligand, the extra d-p back-donation from nickel to the coordinating carbene increases the rigidity of the nickel-ligand bond, and the corresponding angle distortion is more difficult. This makes the concerted cyclic oxidative addition unfavorable with SIMes ligand, and the back-side S(N)2-type oxidative addition delivers the stereoinversion.
CALTECH1/10/2018double catalystsCsp3-ring(s)-Csp2E-EOXOMsBrBenzylVinylNo baseNo BaseWeak0.36_10.1039/c9sc03347e,10.1002/anie.202114556,10.1021/acscatal.0c03993,10.1021/acscatal.9b0052110.1002/ejoc.202101440,10.1002/anie.202115702,10.1021/acscatal.1c05144,10.1002/anie.202113209,10.1002/anie.202114556,10.1021/acscatal.1c04128,10.1038/s41467-021-26843-2,10.1038/s41467-021-26794-8,10.1021/acscatal.1c04314,10.1021/acs.orglett.1c03187,10.1021/acscatal.1c02307,10.1021/jacs.1c08695,10.1021/acscatal.1c03265,10.1021/jacs.1c07139,10.1021/acscatal.1c02851,10.1021/jacs.1c05670,10.1021/jacs.1c03827,10.1039/d1sc02547c,10.1002/cjoc.202100101,10.1021/jacs.1c03527,10.1039/d1sc00822f,10.1039/d1sc00283j,10.1002/anie.202100810,10.1021/jacs.1c00440,10.1021/jacs.1c02117,10.1021/acs.orglett.1c00677,10.1002/anie.202101076,10.1021/acscatal.1c00531,10.1021/jacs.0c12843,10.2174/1570179418666210224124931,10.1055/s-0040-1707342,10.1055/s-0040-1707216,10.1021/acscatal.0c03993,10.1021/acs.orglett.0c03248,10.1021/acscatal.0c03237,10.1002/adsc.202000945,10.1016/j.tet.2020.131493,10.1021/acscatal.0c01842,10.1021/jacs.0c05254,10.1021/acs.orglett.0c01683,10.1021/acs.orglett.0c01284,10.1021/jacs.0c03708,10.1002/anie.201915454,10.1016/j.isci.2020.100985,10.1002/anie.202000016,10.1002/anie.201914175,10.1002/anie.201913743,10.1021/acs.orglett.9b03102,10.1002/anie.201910168,10.1039/c9sc03347e,10.1039/c9cc05385a,10.1002/anie.201906815,10.1021/acs.oprd.9b00232,10.1021/acscatal.9b01785,10.6023/cjoc201901004,10.1039/c9cc00768g,10.1021/acs.orglett.9b01048,10.1021/acs.orglett.9b01097,10.1021/acs.orglett.9b00692,10.1021/acscatal.9b00521,10.1002/anie.201814208,10.1002/anie.201814340,10.6023/cjoc201806038,10.1002/anie.201813222,10.1021/acscatal.8b04481,10.1039/c8sc04162h,10.1039/c8qo01044g,10.1021/acscatal.8b03930,10.1021/acs.orglett.8b03062,10.1021/jacs.8b08605,10.1021/acscatal.8b02784,10.1021/jacs.8b06458,10.1016/j.tet.2018.04.067,10.1021/acs.orglett.8b00114Kelly1/25/2022
281
193FALSEjacs.7b1286510.1021/jacs.7b12865https://sci-hub.wf/10.1021/jacs.7b12865https://doi.org/10.1021/jacs.7b12865NiC-O ActivationShihongTRUE1187892018Rueping, M
Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
An asymmetric Ni-catalyzed reductive cross-coupling has been developed to prepare enantioenriched allylic silanes. This enantioselective reductive alkenylation proceeds under mild conditions and exhibits good functional group tolerance. The chiral allylic silanes prepared here undergo a variety of stereospecific transformations, including intramolecular Hosomi-Sakurai reactions, to set vicinal stereogenic centers with excellent transfer of chirality.
Rhein Westfal TH Aachen
3/14/2018TRUETRUEFALSECsp2-Csp3E-NuOBOCOPh9-BBN
Carbonyl
AlkylCs2CO3Ionic-CO3Strong0.13_xx10.1021/acscatal.9b00884,10.1002/anie.201808560,10.1002/anie.202103327,10.1021/jacs.0c06995,10.1021/acs.orglett.8b01021,10.1038/s41929-020-00560-3,10.1002/anie.20200227110.1002/anie.202201142,10.1039/d1ob02349g,10.1039/d1qo01756j,10.1039/d1sc06968c,10.1002/anie.202114731,10.1002/chem.202102734,10.6023/cjoc202104049,10.1021/acs.joc.1c00613,10.1002/chem.202102130,10.1002/chem.202101880,10.1002/anie.202106356,10.1039/d1qo00824b,10.1039/d1qo00530h,10.1002/chem.202100018,10.1021/acs.orglett.1c01103,10.1002/anie.202103327,10.1021/acs.orglett.1c00940,10.1002/chem.202005397,10.1039/d0cc08389e,10.1002/cctc.202001949,10.1016/j.cclet.2020.04.005,10.1016/j.tet.2020.131912,10.1038/s41929-020-00560-3,10.1002/chem.202004437,10.1021/acssuschemeng.0c08262,10.1021/acs.chemrev.0c00153,10.1021/acs.joc.0c02209,10.1021/acs.joc.0c01720,10.1021/acs.orglett.0c03342,10.1016/j.tetlet.2020.152532,10.1021/acs.organomet.0c00584,10.1002/adsc.202000794,10.1002/anie.202010244,10.1055/s-0040-1705943,10.1016/j.trechm.2020.08.001,10.1021/jacs.0c06995,10.1002/slct.202002787,10.1021/acs.organomet.0c00387,10.1021/acs.chemrev.9b00682,10.1126/sciadv.aba7614,10.1039/d0sc01641a,10.1002/anie.202002271,10.1039/d0ob00789g,10.1021/jacs.0c00283,10.1021/jacs.0c02839,10.1021/acsomega.9b04450,10.1021/jacs.9b13531,10.1021/acs.orglett.0c00542,10.1002/asia.202000117,10.3390/catal10030296,10.1126/science.aba2419,10.1039/c9qo01428d,10.3390/molecules25010230,10.1002/chem.201904842,10.1002/adsc.201901188,10.1021/acs.joc.9b02154,10.1002/anie.201911372,10.1021/acs.joc.9b01103,10.1021/acs.orglett.9b02398,10.1039/c9nj01748h,10.1039/c9sc00892f,10.1039/c9ra02394a,10.1002/cctc.201900254,10.1021/acs.joc.8b03267,10.1021/acs.orglett.9b01053,10.1021/acscatal.9b00884,10.1021/acs.orglett.9b00774,10.1021/acs.inorgchem.8b03425,10.1039/c9dt00450e,10.1021/acs.joc.8b03114,10.1002/anie.201813182,10.1039/c8nj05503c,10.3390/catal9010053,10.1002/anie.201810145,10.1002/anie.201811139,10.1021/acs.joc.8b02180,10.1039/c8sc03430c,10.1016/j.tet.2018.10.025,10.1039/c8ob01832d,10.1021/acs.joc.8b02104,10.1021/acscatal.8b03396,10.1021/acscatal.8b02815,10.3390/molecules23102412,10.1021/acsomega.8b02155,10.1002/anie.201808560,10.1039/c8ob01389f,10.1002/asia.201800478,10.1039/c8cc03954b,10.1021/acs.orglett.8b01582,10.1021/jacs.8b04479,10.1021/acs.orglett.8b01646,10.1002/ajoc.201800207,10.1002/chem.201801887,10.1016/j.chempr.2018.05.012,10.1002/chem.201704670,10.1021/acs.orglett.8b01021,10.1021/acs.orglett.8b01233,10.1021/acs.orglett.8b00930,10.1021/acs.accounts.8b00023,10.1021/acscatal.8b01224,10.1021/jacs.8b02462 Long 11/5/2021MAR 142018FALSEFALSEFALSEFALSE140103724
282
90FALSEjacs.8b0180010.1021/jacs.8b01800https://sci-hub.wf/10.1021/jacs.8b01800https://doi.org/10.1021/jacs.8b01800NiC-O ActivationLongTRUE534382018
Stradiotto, M
Ligand-Controlled Chemoselective C(acyl)-O Bond vs Caryl)-C Bond Activation of Aromatic Esters in Nickel Catalyzed C(sp(2))-C(sp(3)) Cross-Couplings
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
A ligand-controlled and site-selective nickel catalyzed Suzuki-Miyaura cross-coupling reaction with aromatic esters and alkyl organoboron reagents as coupling partners was developed. This methodology provides a facile route for C(sp(2))-C(sp(3)) bond formation in a straightforward fashion by successful suppression of the undesired beta-hydride elimination process. By simply switching the phosphorus ligand, the ester substrates are converted into the alkylated arenes and ketone products, respectively. The utility of this newly developed protocol was demonstrated by its wide substrate scope, broad functional group tolerance and application in the synthesis of key intermediates for the synthesis of bioactive compounds. DFT studies on the oxidative addition step helped rationalizing this intriguing reaction chemoselectivity: whereas nickel complexes with bidentate ligands favor the Caryl)-C bond cleavage in the oxidative addition step leading to the alkylated product via a decarbonylative process, nickel complexes with monodentate phosphorus ligands favor activation of the C(acyl)-O bond, which later generates the ketone product.
Dalhousie Univ4/18/2018Csp2_ar-Osp2E-NuOHOTsHArylORCs2CO3Ionic-CO3Weak0.36_10.1021/acscatal.8b01879,10.1002/anie.202002392,10.1021/acscatal.1c03010,10.1002/anie.20201434010.1002/slct.202103723,10.1039/d1sc06968c,10.1016/j.matpr.2021.09.464,10.1039/d1sc05113j,10.1016/j.jorganchem.2021.122145,10.1021/acs.orglett.1c03172,10.1021/acs.orglett.1c03066,10.1002/cctc.202101013,10.1039/d1qo01078f,10.1021/jacs.1c05661,10.1021/acscatal.1c03010,10.1002/anie.202107820,10.1021/acscatal.1c02790,10.1039/d1gc01902c,10.1038/s41467-021-24031-w,10.1039/d0qo01194k,10.1021/acs.organomet.1c00018,10.1039/d0cc08389e,10.1016/j.ica.2020.120191,10.1021/acs.orglett.0c04310,10.1002/adsc.202001346,10.1002/anie.202014340,10.1021/jacs.0c07381,10.1021/acs.orglett.0c03058,10.6023/cjoc202000059,10.1039/d0dt02063j,10.1021/acs.orglett.0c01668,10.1177/1747519820925376,10.1002/anie.202003359,10.1002/anie.201916398,10.1002/anie.202002392,10.1021/acs.orglett.0c00532,10.1021/acscatal.9b03827,10.1007/s10562-019-03070-5,10.1002/adsc.201901302,10.1021/acs.orglett.9b02858,10.1002/ejic.201900972,10.1002/asia.201900968,10.1039/c9ob01224a,10.1021/jacs.9b02411,10.1039/c9sc00554d,10.1002/chem.201900498,10.1021/jacs.9b01886,10.1021/jacs.8b12142,10.1002/anie.201812862,10.1021/acs.organomet.8b00451,10.1002/anie.201808024,10.1021/acscatal.8b01879,10.1021/acscatal.8b021871/6/2022
283
104FALSEjacs.8b0213410.1021/jacs.8b02134https://sci-hub.wf/10.1021/jacs.8b02134https://doi.org/10.1021/jacs.8b02134NiC-O ActivationLongTRUE601312018Mazet, C
Exploiting Ancillary Ligation To Enable Nickel-Catalyzed C-O Cross-Couplings of Aryl Electrophiles with Aliphatic Alcohols
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
The use of (L)Ni(o-tolyl)Cl precatalysts (L = PAd-DalPhos or CyPAd-DalPhos) enables the C(sp(2))-cross-coupling of primary, secondary, or tertiary aliphatic alcohols with (hetero)aryl electrophiles, induding unprecedented examples of such nickel-catalyzed transformations employing (hetero)aryl chlorides, sulfonates, and pivalates. In addition to offering a competitive alternative to palladium catalysis, this work establishes the feasibility of utilizing ancillary ligation as a complementary means of promoting challenging nickel-catalyzed C(sp(2))-O cross-couplings, without recourse to precious metal photoredox catalytic methods.
Univ Geneva4/4/2018Csp2-Csp2_arE-NuOMgOMeMgXVinylArylNo baseNo BaseStrong-0.28_10.1021/acscatal.9b0052110.1021/acs.orglett.1c04321,10.1021/acscatal.1c05073,10.1021/jacs.1c09705,10.1039/d1cc05347g,10.1002/adsc.202100585,10.1038/s41467-021-25696-z,10.1039/d1cc04370f,10.1021/acs.orglett.1c02143,10.1002/anie.202105800,10.1021/acscatal.1c02144,10.1039/d1sc02575a,10.1246/cl.200793,10.1002/anie.202017190,10.1039/d0cs00449a,10.1002/anie.202011231,10.6023/cjoc202005050,10.1055/s-0040-1707166,10.1002/chem.202002849,10.1038/s41467-020-18658-4,10.1002/ejoc.202001061,10.1002/anie.202008854,10.1021/acs.orglett.0c02236,10.1021/acs.orglett.0c01582,10.1039/d0sc02542a,10.1021/jacs.0c03589,10.1021/acscatal.0c01605,10.1002/anie.202005058,10.1021/acscatal.0c01174,10.1002/adsc.202000210,10.1002/anie.201916014,10.1002/anie.201915864,10.1021/acs.orglett.9b03557,10.1002/anie.201913281,10.1021/jacs.9b09373,10.1021/acs.joc.9b02042,10.1016/j.tetlet.2019.07.029,10.1021/acs.orglett.9b02473,10.1021/acs.organomet.9b00276,10.1002/cjoc.201800554,10.1021/acscatal.8b05072,10.1021/acscatal.9b00688,10.1021/acs.orglett.9b00946,10.1038/s41467-019-09783-w,10.1002/anie.201814558,10.1021/acscatal.9b00521,10.1021/acscatal.9b00118,10.1038/s42004-018-0107-y,10.1038/s41467-018-06240-y,10.1021/acs.orglett.8b02450,10.1002/chem.201803574,10.1039/c8qo00585k,10.1021/acs.joc.8b01288,10.1002/anie.201802434,10.1021/jacs.8b03560 Long 1/6/2022
284
149FALSEjacs.8b1280110.1021/jacs.8b12801https://sci-hub.wf/10.1021/jacs.8b12801https://doi.org/10.1021/jacs.8b12801NiC-O ActivationGerryTRUE100712019Gong, HG
Multicatalytic Stereoselective Synthesis of Highly Substituted Alkenes by Sequential Isomerization/Cross-Coupling Reactions
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Starting from readily available alkenyl methyl ethers, the stereoselective preparation of highly substituted alkenes by two complementary multicatalytic sequential isomerization/cross-coupling sequences is described. Both elementary steps of these sequences are challenging processes when considered independently. A cationic iridium catalyst was identified for the stereoselective isomerization of allyl methyl ethers and was found to be compatible with a nickel catalyst for the subsequent cross -coupling of the in situ generated methyl vinyl ethers with various Grignard reagents. The method is compatible with sensitive functional groups and a multitude of olefinic substitution patterns to deliver products with high control of the newly generated C=C bond. A highly enantioselective variant of this [Ir/Ni] sequence has been established using a chiral iridium precatalyst. A complementary [Pd/Ni] catalytic sequence has been optimized for alkenyl methyl ethers with a remote C=C bond. The final alkenes were isolated with a lower level of stereocontrol. Upon proper choice of the Grignard reagent, we demonstrated that C(sp(2)) C(sp(2)) and C(sp(2)) C(sp(3)) bonds can be constructed with both systems delivering products that would be difficult to access by conventional methods.
Shanghai Univ1/16/2019Csp3-Csp2_arE-EOX
OCOCO2tBu
ClAlkylArylNo baseNo BaseStrong0.13_10.1021/acscatal.1c05208,10.1021/jacs.0c12462,10.1021/jacs.0c13093,10.1021/acs.orglett.9b00174,10.1021/jacs.9b05224,10.1021/jacs.0c06904,10.1021/acscatal.1c0520810.1021/acs.orglett.1c04359,10.1055/s-0040-1719881,10.1002/ejoc.202101440,10.1039/d1gc04001d,10.1055/s-0041-1737762,10.1021/acs.joc.1c02897,10.1021/acscatal.1c05530,10.1021/jacs.1c11623,10.1021/acs.orglett.1c04029,10.1039/d1ra08015f,10.1021/acscatal.1c05208,10.1021/acs.orglett.1c03674,10.1039/d1qo01614h,10.1021/acscatal.1c04239,10.6023/cjoc202106021,10.1021/acs.orglett.1c02893,10.1021/acscatal.1c02307,10.1021/jacs.1c08695,10.1021/acs.orglett.1c02738,10.1038/s41467-021-25702-4,10.1039/d1sc04071e,10.1038/s41586-021-03920-6,10.1039/c9cs00571d,10.1021/jacs.1c04254,10.1021/jacs.1c03827,10.1016/j.tetlet.2021.153129,10.1021/acscatal.1c01416,10.1002/ejoc.202100344,10.1039/d1sc01349a,10.1039/d1sc00133g,10.1055/a-1467-2432,10.1021/jacs.1c00618,10.1039/d0cs01107j,10.1021/acs.orglett.1c00431,10.1002/anie.202014991,10.1039/d0sc06586b,10.1021/jacs.0c13093,10.1002/ejoc.202001602,10.1039/d0ra10739e,10.1021/acs.orglett.1c00023,10.1021/acs.orglett.0c04039,10.1021/jacs.0c12462,10.1055/s-0040-1707342,10.1021/jacs.0c11172,10.1055/a-1328-0352,10.1021/acscatal.0c03237,10.1038/s41467-020-19194-x,10.1021/jacs.0c07492,10.1038/s41467-020-18658-4,10.1021/acs.accounts.0c00291,10.1021/jacs.0c06904,10.1039/d0cc00457j,10.1021/acs.orglett.0c01612,10.1038/s41467-020-17224-2,10.1021/acs.orglett.0c01365,10.1021/jacs.0c02673,10.1039/d0sc01471k,10.1021/jacs.0c02237,10.1002/anie.202001571,10.6023/cjoc201911016,10.1021/acs.orglett.0c00561,10.1002/ajoc.202000007,10.1002/chem.201905224,10.3390/molecules25030602,10.1039/c9cc07072a,10.1021/acs.joc.9b02431,10.1002/chem.201905048,10.1002/asia.201901490,10.1039/c9sc03765a,10.1021/acs.joc.9b01387,10.1002/anie.201909852,10.1016/j.tet.2019.06.034,10.1021/jacs.9b05224,10.1021/acs.oprd.9b00232,10.1021/acs.orglett.9b01987,10.1002/anie.201904028,10.1021/acs.orglett.9b01048,10.1021/jacs.9b02844,10.1021/acs.orglett.9b01097,10.1021/acs.orglett.9b00174Kelly1/20/2022
285
301FALSEol048490d10.1021/ol048490dhttps://sci-hub.wf/10.1021/ol048490dhttps://doi.org/10.1021/ol048490dNiC-N ActivationYizhouTRUE1045#N/A2004Liu, JQ
Azoles as Suzuki cross-coupling leaving groups: Syntheses of 6-arylpurine 2 '-deoxynucleosides and nucleosides from 6-(imidazol-1-yl)- and 6-(1,2,4-triazol-4-yl)purine derivativesORG LETT
6-(Imidazol-1-yl)-, 6-(benzimidazol-1-yl)-, and 6-(1,2,4-triazol-4-yl)purine nucleosides undergo a nickel-mediated C-C cross-coupling of azole-substituted purine derivatives with arylboronic acids to give good yields of 6-arylpurine nucleosides.
Brigham Young Univ9/16/2004TRUETRUEFALSECsp2_ar-Csp2_arE-NuNBImB(OH)2HetArylK3PO4Ionic-PO4E-H_xx10.1021/jo4005537,10.1002/anie.200900329,10.1002/anie.201102092,10.1038/ncomms12937,10.1021/ol901978e10.1007/s00044-021-02700-1,10.1021/acscatal.0c03334,10.1039/d0ob00563k,10.1021/acs.organomet.9b00672,10.1016/j.tet.2019.130777,10.3390/molecules24213812,10.1002/slct.201902137,10.1039/c8ob02992j,10.1039/c8ob00305j,10.1021/acs.orglett.8b00545,10.1021/jacs.7b08579,10.1007/s10934-017-0381-6,10.1002/ejoc.201700406,10.1039/c6nj03718f,10.1039/c7ra02549a,10.1002/slct.201600962,10.1038/ncomms12937,10.1016/j.jorganchem.2016.02.005,10.1039/c6cy00597g,10.1039/c6dt02995g,10.1021/acs.chemrev.5b00386,10.1016/j.tet.2015.05.068,10.1002/ejoc.201403527,10.1021/cs5014927,10.1039/c5ra17740e,10.1039/c5ra04406e,10.1039/c4ra16468g,10.1021/jo502123k,10.1016/j.ejmech.2014.07.110,10.1021/ol501180q,10.1002/ejoc.201400126,10.1021/ja501649a,10.1002/aoc.3126,10.1021/jo500026g,10.2174/1385272819666140714174457,10.1002/cssc.201300485,10.1016/j.molcata.2013.10.014,10.1021/jo401915t,10.1002/ajoc.201300172,10.1021/jo401032r,10.1021/jo4005537,10.1002/aoc.2964,10.1039/c3cs35521g,10.1039/c3dt00086a,10.1021/ja308950d,10.1021/om300399j,10.1016/j.ica.2012.02.033,10.1039/c2dt31174g,10.1039/c2cc33755j,10.1039/c2gc35419e,10.1021/ol202862t,10.1002/aoc.1847,10.1016/j.jorganchem.2011.01.003,10.1021/cr1002276,10.1002/anie.201102092,10.1016/j.bmcl.2010.10.141,10.1021/om1000327,10.1021/jo1010334,10.1016/j.bmc.2010.07.017,10.1021/om9010406,10.1002/anie.200901317,10.1021/ol901978e,10.1021/cr900074m,10.1002/ejoc.200801004,10.1002/anie.200900329,10.1002/anie.200903146,10.1039/b903285a,10.1021/om800711g,10.1021/ja804804p,10.1016/j.tetlet.2008.02.139,10.1002/anie.200801447,10.1021/om700796g,10.1021/om700607m,10.1002/ejoe.200700171,10.1021/jo070843+,10.1021/ja0713431,10.1021/jo061759h,10.1055/s-2006-950240,10.1016/j.ccr.2006.02.031,10.1021/jo060340o,10.1016/j.tet.2005.11.072,10.1002/anie.200504565,10.1135/cccc20061029,10.1021/jo0513764,10.1021/om050224w,10.1021/ol051573p,10.1021/jo051110x,10.1021/jo0503557,10.1021/ol050063s11/3/2021FALSE
286
71FALSEjacs.8b1340310.1021/jacs.8b13403https://sci-hub.wf/10.1021/jacs.8b13403https://doi.org/10.1021/jacs.8b13403NiC-O ActivationJaniceTRUE501#N/A2019XuJin, Z
Zn-Mediated Fragmentation of Tertiary Alkyl Oxalates Enabling Formation of Alkylated and Arylated Quaternary Carbon Centers
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Zn-mediated reduction of readily accessible dialkyl oxalates derived from tertiary alcohols provides an efficient approach to C-O bond fragmentation and alkyl radical formation. With MgCl2 as the indispensable additive and Ni as the promoter, trapping the radical with activated alkenes and aryl-Ni intermediates allows for the generation of alkylated and arylated all-carbon quaternary centers.
Nankai Univ2/6/2019TRUEFALSEFALSECsp2_ar-Csp2_arE-NuOB
2-(4,6-dimethoxy-1,3,5-triazin-2-yl)benzonitrile
B(OH)2ArylArylK3PO4Ionic-PO4Strong-0.32_10.1021/jacs.1c12654,10.1021/acs.orglett.1c04000,10.1039/d1qo01078f,10.1021/acs.orglett.1c02460,10.1002/anie.202105631,10.1039/d1qo00140j,10.1055/a-1485-5156,10.1039/d0cs00447b,10.1039/d0sc05555g,10.1021/acs.orglett.1c00245,10.1016/j.ccr.2020.213683,10.1021/acscatal.0c05481,10.1002/adsc.202001053,10.1021/acs.orglett.0c03819,10.1021/acs.orglett.0c03377,10.1021/acs.orglett.0c03757,10.1021/jacs.0c09545,10.1039/d0qo00820f,10.1021/acs.orglett.0c02528,10.1021/acs.joc.0c01392,10.1002/chem.202001757,10.1039/d0cc02851g,10.1039/d0sc02439b,10.1021/jacs.0c04074,10.1002/bkcs.12044,10.1016/j.cclet.2019.09.057,10.6023/cjoc201909015,10.1016/j.tet.2020.130925,10.1002/anie.201915624,10.1002/jccs.201900471,10.6023/cjoc201903029,10.1038/s41467-019-13098-1,10.1107/S2053229619012567,10.1021/acs.joc.9b01851,10.1039/c9cc05807a,10.1021/acs.orglett.9b02910,10.1021/jacs.9b07887,10.1002/cssc.201901951,10.1021/acs.orglett.9b02392,10.1039/c9cc02199j11/11/2021FEB 62019FALSEFALSEFALSEFALSE14151903
287
303FALSEol702058e10.1021/ol702058ehttps://sci-hub.wf/10.1021/ol702058ehttps://doi.org/10.1021/ol702058eNiC-H ActivationLongTRUE1071#N/A2007Ju, J
AminoCarbonylation of aryl halides using a nickel phosphite catalytic systemORG LETT
The nickel and phosphite catalytic system with sodium methoxide enables a very efficient aminoCarbonylation reaction to be performed between aryl iodides or bromides and N,N-dimethylformamide (DMF). Phosphite ligand 1, which is very stable to air and moisture and, furthermore, inexpensive, afforded the highest reaction yield.
Chonnam Natl Univ10/25/2007Csp2_ar-Csp2E-NuXHBrHAryl
Carbonyl
NaOMeIonic-OR_10.1021/jo901065y10.3390/catal11121531,10.1002/hlca.202100162,10.1039/d1ob01592c,10.1021/acs.orglett.1c01200,10.1002/slct.202004745,10.1016/j.catcom.2020.106150,10.1016/j.tetlet.2020.152506,10.1021/acs.joc.0c01320,10.1002/adsc.202000586,10.1021/acscatal.9b02635,10.1002/aoc.5174,10.1002/ejoc.201900021,10.1002/chem.201900271,10.1021/acs.chemrev.8b00507,10.1016/j.apcatb.2017.12.058,10.1002/slct.201803311,10.1039/c8ob02322k,10.1007/s10562-018-2519-9,10.1002/sIct.201801297,10.1627/jpi.61.1,10.1039/c7nj03123h,10.1039/c7cc08074c,10.1002/ajoc.201700464,10.1021/acs.joc.7b01028,10.1021/acs.inorgchem.7b01576,10.1021/acs.joc.7b01429,10.1039/c7ob00855d,10.1016/j.tetlet.2017.05.051,10.6023/cjoc201612040,10.1039/c7qo00001d,10.1002/anie.201608433,10.1039/c7ra08009c,10.1016/j.tet.2016.10.043,10.1002/ejoc.201600401,10.1002/slct.201600871,10.1002/ejoc.201501607,10.1016/j.tetlet.2016.01.058,10.1002/adsc.201500874,10.1016/j.tetlet.2015.12.060,10.1021/acscatal.5b02881,10.1002/ejoc.201501349,10.1039/c6ra18679c,10.1039/c5gc02985f,10.1002/cctc.201500824,10.1002/adsc.201500551,10.1002/ejoc.201500734,10.1080/17518253.2015.1065349,10.1021/cs501822r,10.1071/CH15459,10.1039/c5nj00655d,10.1039/c4cc10140e,10.1039/c4ra17015f,10.1016/j.cclet.2014.09.007,10.1039/c4ra15140b,10.1039/c5cy00691k,10.1016/j.tetlet.2014.07.083,10.1016/j.tet.2014.07.009,10.1002/adsc.201400201,10.1055/s-0033-1341046,10.1055/s-0033-1340733,10.1016/j.tetlet.2014.03.069,10.1016/j.tetlet.2013.12.062,10.1021/ol403040g,10.1039/c4ra04673k,10.1039/c3gc41548a,10.1039/c4cc00621f,10.1039/c3ob41855c,10.1016/j.tetlet.2013.09.016,10.1002/ejoc.201301170,10.1021/ol4023886,10.1016/j.tet.2013.06.078,10.1002/ejoc.201300543,10.1039/c3ob40787j,10.1002/ejoc.201201544,10.1016/j.tet.2012.10.002,10.1039/c3ra41000e,10.1039/c3cc41188e,10.1039/c3ob40094h,10.1039/c2cc36417d,10.1016/j.tet.2012.08.065,10.1002/ejoc.201201160,10.1016/j.tetlet.2012.09.039,10.1002/chem.201201203,10.1246/cl.2012.298,10.1016/j.molcata.2011.10.021,10.1002/anie.201108763,10.1002/anie.201200859,10.1002/ejoc.201101000,10.1246/cl.2011.904,10.1055/s-0030-1260060,10.1021/jo200754v,10.1002/anie.201105020,10.1021/jo101611g,10.1016/j.tet.2010.09.037,10.1016/j.inoche.2010.07.028,10.1021/jo1002592,10.1021/jo901065y,10.1055/s-0029-1216822,10.1021/ol900327x,10.1021/ja901153s,10.1021/jo802036m,10.1002/anie.200903957,10.1016/j.tet.2008.08.022,10.1016/j.tetlet.2008.02.04912/28/2021
288
33FALSEjacs.9b0009710.1021/jacs.9b00097https://sci-hub.wf/10.1021/jacs.9b00097https://doi.org/10.1021/jacs.9b00097NiC-O ActivationLongTRUE272382019Hong, X
Sequential Functionalization of meta-C-H and ipso-C-O Bonds of Phenols
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
The use of a template as a linchpin motif in directed remote C-H functionalization is a versatile yet relatively underexplored strategy. We have developed a template-directed approach to realizing one-pot sequential palladium-catalyzed meta-selective C-H olefination of phenols, and nickel-catalyzed ipso-C-O activation and arylation. Thus, this bifunctional template converts phenols to synthetically useful 1,3-disubstituted arenes.
Zhejiang Univ4/10/2019TRUEFALSEFALSExxCsp3-Csp3E-NuOMg
O(Ring-Opening)
MgXAlkylAlkylNo baseNo BaseWeak1_x10.1021/jacs.0c01330,10.1021/jacs.1c0389810.1021/acs.orglett.1c04268,10.1021/acscatal.1c04235,10.6023/cjoc202106021,10.1021/acscatal.1c02307,10.3390/molecules26195947,10.1021/jacs.1c03898,10.1021/acs.inorgchem.1c00145,10.1039/d1qo00370d,10.1021/acs.accounts.1c00050,10.1021/acs.organomet.0c00775,10.1055/s-0040-1706013,10.1055/s-0040-1705987,10.1039/d0ra07472a,10.1016/j.mcat.2020.111045,10.1002/ejoc.202000477,10.1021/acs.orglett.0c01284,10.1021/jacs.0c01330,10.1055/s-0039-1690718,10.1039/c9cc09497k,10.1021/acs.joc.9b02603,10.1002/chem.202000215,10.1016/j.tetlet.2019.151454,10.1016/j.trechm.2019.08.004,10.1021/jacs.9b100261/4/2022APR 102019FALSEFALSEFALSEFALSE141145835
289
32FALSEjacs.9b0275110.1021/jacs.9b02751https://sci-hub.wf/10.1021/jacs.9b02751https://doi.org/10.1021/jacs.9b02751NiC-O ActivationGerry16-FebTRUE272892019Chatani, N
A Unified Explanation for Chemoselectivity and Stereospecificity of Ni-Catalyzed Kumada and Cross-Electrophile Coupling Reactions of Benzylic Ethers: A Combined Computational and Experimental Study
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Ni-catalyzed C(sp(3))-O bond activation provides a useful approach to synthesize enantioenriched products from readily available enantioenriched benzylic alcohol derivatives. The control of stereospecificity is key to the success of these transformations. To elucidate the reversed stereospecificity and chemoselectivity of Ni-catalyzed Kumada and cross-electrophile coupling reactions with benzylic ethers, a combined computational and experimental study is performed to reach a unified mechanistic understanding. Kumada coupling proceeds via a classic cross-coupling mechanism. Initial rate-determining oxidative addition occurs with stereoinversion of the benzylic stereogenic center. Subsequent transmetalation with the Grignard reagent and syn-reductive elimination produce the Kumada coupling product with overall stereoinversion at the benzylic position. The cross-electrophile coupling reaction initiates with the same benzylic C-O bond cleavage and transmetalation to form a common benzylnickel intermediate. However, the presence of the tethered alkyl chloride allows a facile intramolecular S(N)2 attack by the benzylnickel moiety. This step circumvents the competing Kumada coupling, leading to the excellent chemoselectivity of cross-electrophile coupling. These mechanisms account for the observed stereospecificity of the Kumada and cross-electrophile couplings, providing a rationale for double inversion of the benzylic stereogenic center in cross-electrophile coupling. The improved mechanistic understanding will enable design of stereoselective transformations involving Ni-catalyzed C(sp(3))-O bond activation.
Osaka Univ5/8/2019Csp2_ar-Nsp3E-EOCsp2
OCONMe2
Phenyl Formate
Aryl
Morpholine
No baseNo BaseMedium0.31_10.1021/jacs.1c09797,10.1038/s41467-020-20725-910.1021/jacs.1c09797,10.1007/s12274-021-3694-3,10.1039/d1sc03366b,10.1002/jccs.202100046,10.1021/acssuschemeng.0c08262,10.1038/s41467-020-20725-9,10.1021/acs.chemrev.0c00088,10.1016/j.chempr.2020.06.020,10.1021/acs.orglett.0c02320,10.1016/j.mcat.2020.110915,10.1021/jacs.0c05730,10.1039/d0ob00880j,10.1021/acs.orglett.0c01905,10.1021/acs.joc.0c00009,10.1039/c9qo01073d,10.1002/chem.201904288,10.1021/acs.orglett.9b02858,10.1021/acs.orglett.9b03170,10.1021/acs.orglett.9b02504,10.1002/anie.201906264,10.1021/acs.orglett.9b01989,10.1002/chem.2019008221/14/2022
290
47FALSEjacs.9b0328010.1021/jacs.9b03280https://sci-hub.wf/10.1021/jacs.9b03280https://doi.org/10.1021/jacs.9b03280NiC-O ActivationLongTRUE352152019Newman, SG
Nickel-Catalyzed Decarboxylation of Aryl Carbamates for Converting Phenols into Aromatic Amines
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Herein, we describe a new catalytic approach to accessing aromatic amines from an abundant feedstock, namely phenols. The most reliable catalytic method for converting phenols to aromatic amines uses an activating group, such as a trifluoromethane sulfonyl group. However, this activating group is eliminated as a leaving group during the amination process, resulting in significant waste. Our nickel-catalyzed decarboxylation reaction of aryl carbamates forms aromatic amines with carbon dioxide as the only byproduct. As this amination proceeds in the absence of free amines, a range of functionalities, including a formyl group, are compatible. A bisphosphine ligand immobilized on a polystyrene support (PS-DPPBz) is key to the success of this reaction, generating a catalytic species that is significantly more active than simple nonsupported variants.
Univ Ottawa5/1/2019TRUEFALSEFALSEyyCsp2_ar-Csp2_arE-EOOOTfOHArylArylTMPNitrogenNitrogen(neutral)Weak0.53_xxxx10.1021/jacs.1c06614,10.1002/anie.20201204810.1002/anie.202201142,10.1002/chem.202103653,10.1002/aoc.6549,10.1002/chem.202102805,10.1021/jacs.1c05661,10.1021/jacs.1c07230,10.1039/d1sc03712a,10.1039/d1cc03261e,10.1021/jacs.1c06614,10.1039/d1nj02508b,10.1002/anie.202103686,10.1021/acscatal.1c00951,10.1039/d0cc08389e,10.1021/acs.orglett.0c03786,10.1039/d0gc02341h,10.1002/anie.202012048,10.1021/acscatal.0c03343,10.1039/d0cc03966g,10.1002/cjoc.202000019,10.1002/anie.202006489,10.1039/d0nj02630a,10.1016/j.tetlet.2020.152254,10.1021/acs.orglett.0c02340,10.6023/cjoc202004028,10.1021/acscatal.0c02105,10.1039/d0gc00383b,10.1039/d0ob00881h,10.1021/acs.joc.9b03346,10.1038/s41467-019-14016-1,10.1002/chem.201903668,10.1002/anie.201906000,10.1002/ejoc.201900769,10.1021/jacs.9b0311311/9/2021MAY 12019FALSEFALSEFALSEFALSE141176869
291
173FALSEjacs.9b0386310.1021/jacs.9b03863https://sci-hub.wf/10.1021/jacs.9b03863https://doi.org/10.1021/jacs.9b03863NiC-O ActivationGerryTRUE111402019Shu, XZ
Ketone Synthesis by a Nickel-Catalyzed Dehydrogenative Cross-Coupling of Primary Alcohols
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
An intermolecular coupling of primary alcohols and organotriflates has been developed to provide ketones by the action of a Ni(0) catalyst. This oxidative transformation is proposed to occur by the union of three distinct catalytic cycles. Two competitive oxidation processes generate aldehyde in situ via hydrogen transfer oxidation or (pseudo)dehalogenation pathways. As aldehyde forms, a Ni-catalyzed carbonyl-Heck process enables formation of the key carbon-carbon bond. The utility of this rare alcohol to ketone transformation is demonstrated through the synthesis of diverse complex and bioactive molecules.
Lanzhou Univ5/8/2019TRUETRUETRUEyCsp2-Csp2_arE-EOXOTfIVinylArylNo baseNo BaseWeak0.53_xx10.1021/jacs.0c12462,10.1002/anie.202011036,10.1039/c9sc03347e,10.1039/d1cc00634g10.1002/anie.202200215,10.1021/acs.orglett.2c00029,10.1002/anie.202115702,10.1002/cjoc.202100819,10.1021/acscatal.1c04533,10.1002/anie.202113209,10.1021/acs.orglett.1c03739,10.1039/d1cc04996h,10.1021/acscatal.1c04235,10.1021/acscatal.1c04128,10.1038/s41467-021-26794-8,10.1021/acscatal.1c04143,10.6023/cjoc202100076,10.1021/jacs.1c08695,10.1021/acs.orglett.1c02887,10.1021/jacs.1c05670,10.1021/jacs.1c06271,10.1021/acs.orglett.1c02270,10.1021/acscatal.1c02277,10.1021/acs.orglett.1c01871,10.1021/jacs.1c03827,10.1021/acs.orglett.1c01649,10.1016/j.tetlet.2021.153129,10.1002/cjoc.202100034,10.1021/acs.orglett.1c00974,10.1002/anie.202102769,10.1021/jacs.1c03527,10.1002/chem.202101082,10.1039/d1sc00943e,10.1039/d1sc01115d,10.1039/d0qo01462a,10.1002/anie.202101076,10.1021/jacs.1c00142,10.1039/d1ob00195g,10.1039/d1cc00634g,10.1055/a-1406-0484,10.1055/a-1353-7605,10.1021/jacs.0c12462,10.1021/acs.orglett.0c03947,10.1055/s-0040-1706000,10.1055/s-0040-1707342,10.1002/anie.202010737,10.1002/anie.202011036,10.1002/anie.202011491,10.1055/s-0040-1707216,10.1021/jacs.0c09949,10.1021/acs.orglett.0c03210,10.1021/acscatal.0c03237,10.1021/acscatal.0c03127,10.1002/adsc.202000537,10.1039/d0qo00632g,10.1021/jacs.0c07126,10.1055/s-0040-1707900,10.1021/acs.orglett.0c02091,10.3390/catal10091084,10.1039/d0sc02054k,10.1021/acscatal.0c01842,10.1021/acscatal.0c02115,10.1021/jacs.0c05254,10.1002/cjoc.202000224,10.1021/acs.orglett.0c01683,10.1038/s41467-020-17085-9,10.1021/jacs.0c03708,10.1002/anie.202003288,10.1002/anie.202000859,10.1055/s-0039-1691525,10.1021/acs.accounts.0c00032,10.1021/acs.orglett.0c00688,10.1038/s42004-020-0292-3,10.1055/s-0039-1690807,10.1039/d0qo00072h,10.1016/j.chempr.2019.12.026,10.1002/ajoc.202000007,10.1002/anie.201914175,10.1021/jacs.9b12554,10.1002/anie.201913733,10.1002/anie.201911012,10.1002/anie.201913367,10.1002/anie.201913743,10.1021/acs.orglett.9b03517,10.1021/acs.orglett.9b03147,10.1021/jacs.9b10026,10.1021/jacs.9b09245,10.1039/c9sc03347e,10.1021/acscatal.9b03172,10.1002/anie.201908029,10.1039/c9qo00744j,10.1021/acs.orglett.9b02788,10.1021/acs.orglett.9b02870,10.1021/acs.orglett.9b02577,10.1002/anie.201907840,10.1002/anie.201906954,10.1021/acs.orglett.9b02130Kelly12/29/2021MAY 82019FALSEFALSEFALSEFALSE141187637
292
138FALSEjacs.9b0546110.1021/jacs.9b05461https://sci-hub.wf/10.1021/jacs.9b05461https://doi.org/10.1021/jacs.9b05461NiC-O ActivationLongTRUE8111382019Weix, DJ
Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Enantioselective cross-electrophile reactions remain a challenging subject in metal catalysis, and with respect to data, studies have mainly focused on stereoconvergent reactions of racemic alkyl electrophiles. Here, we report an enantioselective cross-electrophile aryl-alkenylation reaction of unactivated alkenes. This method provides access to a number of biologically important chiral molecules such as dihydrobenzofurans, indolines, and indanes. The incorporated alkenyl group is suitable for further reactions that can lead to an increase under mild conditions at room temperature, and an easily accessible chiral pyrox ligand is used to afford products with high enantioselectivity. The synthetic utility of this method is demonstrated by enabling the modification of complex molecules such as peptides, indometacin, and steroids.
Univ Wisconsin7/17/2019FALSEFALSETRUECsp2_ar-Csp2_arE-EOOOTfOTsArylArylNo baseNo BaseWeak0.53_xx10.1021/jacs.0c01330,10.1021/acscatal.1c03010,10.1002/anie.202002271,10.1021/acscatal.0c03993,10.1021/jacs.0c06995,10.1002/anie.202200352,10.1021/jacs.0c04670,10.1021/jacs.0c12462,10.1002/anie.202002392,10.1021/jacs.9b11208,10.1002/anie.20201434010.1002/anie.202200352,10.1002/adsc.202101388,10.1021/acscatal.1c05386,10.1021/acscatal.1c05386,10.1021/acscatal.1c05144,10.1021/acscatal.1c04533,10.1021/jacs.1c10907,10.1039/d1cc05691c,10.1002/adsc.202101285,10.3390/molecules26237148,10.1039/d1qo01406d,10.1002/ajoc.202100641,10.1021/acscatal.1c04128,10.1039/d1ob01944a,10.1039/d1qo01474a,10.1039/d1ob01874d,10.1002/asia.202101004,10.1021/acscatal.1c02307,10.1021/acs.accounts.1c00480,10.1021/acscatal.1c02952,10.1055/a-1608-5693,10.1002/anie.202106273,10.1021/acscatal.1c03010,10.1039/d1sc03712a,10.1021/jacs.1c05988,10.1039/c9cs00571d,10.1021/jacs.1c04215,10.1021/acs.orglett.1c01213,10.1021/acscatal.1c01416,10.1039/d1ob00521a,10.1055/a-1507-4153,10.1021/acs.joc.1c00452,10.1021/acscatal.1c01102,10.1039/d1sc01028j,10.1021/acs.orglett.1c00313,10.1039/d0sc05425a,10.1002/chem.202004437,10.1021/jacs.0c12462,10.1039/d0ra08737h,10.1021/acs.organomet.0c00628,10.1021/acs.orglett.0c03939,10.1080/14756366.2021.1900165,10.1002/anie.202014340,10.1021/acscatal.0c03993,10.1021/acscatal.0c03237,10.1002/adsc.202000985,10.1039/d0sc03217d,10.1021/acs.chemrev.0c00088,10.1021/jacs.0c06995,10.1021/acs.orglett.0c02429,10.1021/acs.joc.0c00929,10.1021/acs.orglett.0c02165,10.1038/s41467-020-17939-2,10.1021/jacs.0c05730,10.1021/acs.orglett.0c01580,10.1021/acs.oprd.0c00134,10.1021/jacs.0c04670,10.1002/anie.202002271,10.1021/jacs.0c02673,10.1007/s11164-020-04145-4,10.1021/jacs.0c00283,10.1002/anie.202002392,10.1021/jacs.0c01330,10.1021/jacs.9b11507,10.1021/jacs.9b12328,10.1021/jacs.9b11208,10.1134/S1070363219120405,10.1021/acscatal.9b03366,10.1002/anie.201906815Kelly11/11/2021JUL 172019FALSEFALSEFALSEFALSE1412810978
293
231FALSEjo00041a00410.1021/jo00041a004https://sci-hub.wf/10.1021/jo00041a004https://doi.org/10.1021/jo00041a004NiC-O ActivationTRUE17022621992
SENGUPTA, S
LiCl-Accelerated Multimetallic Cross-Coupling of Aryl Chlorides with Aryl Triflates
JOURNAL OF ORGANIC CHEMISTRY
While the synthesis of biaryls has advanced rapidly in the past decades, cross-Ullman couplings of aryl chlorides, the most abundant aryl electrophiles, have remained elusive. Reported here is the first general cross-Ullman coupling of aryl chlorides with aryl triflates. The selectivity challenge associated with coupling an inert electrophile with a reactive one is overcome using a multimetallic strategy with the appropriate choice of additive. Studies demonstrate that LiCl is essential for effective cross-coupling by accelerating the reduction of Ni(II) to Ni(0) and counteracting autoinhibition of reduction at Zn(0) by Zn(II) salts. The modified conditions tolerate a variety of functional groups on either coupling partner (42 examples), and examples include a three-step synthesis of flurbiprofen.
UNIV WATERLOO,GUELPH WATERLOO CTR GRAD WORK CHEM,WATERLOO N2L 3G1,ONTARIO,CANADA.
7/17/1992Csp2_ar-Csp2_arE-NuOMgOTfMgXArylArylNo baseNo BaseWeak0.53_10.1021/jacs.7b04973,10.1021/ol9028308,10.1021/cs501045v,10.1002/anie.200453765,10.1021/ja907700e,10.1002/anie.201402922,10.1021/ol9029534,10.1016/S0040-4039(99)00439-6,10.1002/anie.201806790,10.1021/ja200398c,10.1002/chem.201103784,10.1021/ol4011757,10.1021/acscatal.9b00744,10.1021/ja906477r,10.1021/acscatal.1c04800,10.1016/S0022-328X(02)01174-9,10.1021/ol401727y,10.1021/ol050393c,10.1246/cl.2011.913,10.1021/ol301847m,10.1021/ja903091g,10.1021/jo00106a03110.1021/acscatal.1c04800,10.1055/a-1349-3543,10.1055/a-1306-3228,10.1021/acs.chemrev.0c00088,10.1021/acs.orglett.0c01937,10.1039/d0sc01585g,10.1021/acs.orglett.0c01123,10.1002/cjoc.201900506,10.1021/acs.orglett.0c00094,10.1002/ejoc.201901140,10.1016/j.jcat.2019.07.026,10.1039/c9dt00455f,10.1002/anie.201901724,10.1021/acscatal.9b00744,10.1002/hlca.201800242,10.1021/acs.orglett.8b03417,10.1007/3418_2018_19,10.1016/j.tet.2018.10.025,10.1055/s-0037-1610273,10.1055/s-0037-1611053,10.1002/jhet.3280,10.1002/anie.201806790,10.1021/acscatal.8b02009,10.1016/j.jorganchem.2018.01.019,10.1021/acs.orglett.8b00755,10.1021/acs.organomet.8b00046,10.1002/cjoc.201700664,10.1002/ejoc.201701142,10.1055/s-0036-1589093,10.1055/s-0036-1590985,10.1002/anie.201706581,10.1021/jacs.7b04973,10.1038/s41570-017-0025,10.1021/acs.organomet.7b00030,10.1021/acscatal.6b02964,10.1002/chem.201601584,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1016/j.tet.2016.02.069,10.1016/bs.adomc.2016.07.001,10.1039/c5ra27859g,10.1021/acs.joc.5b01300,10.1021/acs.joc.5b01540,10.1016/j.tetlet.2015.07.033,10.1002/ejoc.201500630,10.1021/acs.organomet.5b00351,10.1002/adsc.201500304,10.1021/jo502561m,10.1039/C5QO00243E,10.1002/anie.201402922,10.1016/j.ica.2014.08.012,10.1021/ol5024344,10.1021/cs501045v,10.1038/nature13274,10.1021/ol500707w,10.1021/ja4118413,10.1039/c4ra04398g,10.1595/147106713X672311,10.1055/s-0033-1339643,10.1021/ol401727y,10.1021/ol4011757,10.1021/jo4002382,10.1007/3418_2012_42,10.1039/c3cs35521g,10.1002/ejoc.201200914,10.1021/op300236f,10.1039/c3ra44884c,10.1002/adsc.201200364,10.1021/ol301847m,10.1021/ol301681z,10.1021/jo300713h,10.1021/ol300908g,10.1021/ol301275u,10.1002/chem.201103784,10.1039/c1cc15845g,10.1246/cl.2011.913,10.1246/cl.2011.1001,10.1002/adsc.201000975,10.1021/ja200398c,10.1021/cr100259t,10.1002/chem.201001943,10.1002/chem.201002273,10.1021/ar100082d,10.1021/ol1018739,10.1021/ja100783c,10.1021/ol9029534,10.1021/ol9028308,10.1021/ja906477r,10.1021/ja907700e,10.1021/ja907281f,10.1021/ja903091g,10.1002/ejoc.200900252,10.1021/jm070678q,10.1055/s-2007-983845,10.1134/S107042800705017X,10.1021/jo062148s,10.1039/b618617c,10.1021/jo0520994,10.1021/ja056327n,10.1021/ol051896l,10.1021/ol050393c,10.1016/j.jorganchem.2004.10.037,10.1002/anie.200462013,10.1002/anie.200500099,10.1055/s-2004-834878,10.1021/jo049454v,10.1055/s-2004-831317,10.1002/anie.200352633,10.1002/anie.200453765,10.1016/j.tet.2003.06.001,10.1016/S0040-4039(03)01804-5,10.1016/S0040-4020(03)00761-0,10.1016/S0040-4039(03)00786-X,10.1021/ja021244h,10.1021/jo026449n,10.1016/S0040-4039(03)00075-3,10.1039/b305043b,10.1021/jo026136s,10.1055/s-2002-32945,10.1016/S0022-328X(02)01174-9,10.1016/S0957-4166(01)00199-9,10.1021/ol005694v,10.1021/ol9907872,10.1002/jhet.5570360608,10.1021/jo990316t,10.1016/S0040-4020(99)00176-3,10.1016/S0040-4039(99)00439-6,10.1016/S0040-4039(99)00247-6,10.1016/S0040-4039(98)02670-7,10.1016/S0040-4020(98)00603-6,10.1016/S0040-4039(98)00996-4,10.1021/jo971771x,10.1016/S0040-4020(97)10217-4,10.1016/S0040-4020(97)10233-2,10.1016/S0040-4039(97)01655-9,10.1021/jo960058p,10.1021/jo961464b,10.1021/jo00106a031,10.1351/pac199466102155,10.1016/0022-328X(94)88094-8,10.1039/p19940002273,10.1080/10406639408015152,10.5059/yukigoseikyokaishi.51.1087,10.1021/jo00059a059,10.1016/0040-4039(93)85089-F,10.1080/00397919308011138Kelly1/6/2022
294
224FALSEjo00106a03110.1021/jo00106a031https://sci-hub.wf/10.1021/jo00106a031https://doi.org/10.1021/jo00106a031NiC-O ActivationLongTRUE150151061995Percec, V
NI(0)-CATALYZED CROSS COUPLING OF ARYL O-CARBAMATES AND ARYL TRIFLATES WITH GRIGNARD-REAGENTS - DIRECTED ORTHOMETALLATION-ALIGNED SYNTHETIC METHODS FOR POLYSUBSTITUTED AROMATICS VIA A 1,2-DIPOLE EQUIVALENT
JOURNAL OF ORGANIC CHEMISTRY
The first Ni(0)-catalyzed cross-coupling reactions of aryl O-carbamates and aryl triflates with Grignard reagents (Scheme I) to give diversely polysubstituted aromatics 2d and 2e (Table I) which feature regiospecificity based on directed ortho metalation (carbamate), minimal beta-hydride elimination (triflate), and dependence on steric and electronic effects are described.
CASE WESTERN RESERVE UNIV,DEPT MACROMOLEC SCI,W M KECK LABS ORGAN SYNTH,CLEVELAND,OH 44106
1/13/1995Csp2_ar-Csp2_arE-EOOOTfOTfArylArylEt4NINitrogenNitrogen(charged)Weak0.53_x10.1016/j.tetlet.2006.01.145,10.1002/adsc.201400460,10.1002/ejoc.200900067,10.1021/ol801972f,10.1002/anie.200803814,10.1021/jo00126a047,10.1021/jo300209d,10.1039/c7cc01932g,10.1021/jo00109a045,10.1021/jacs.9b11208,10.1016/S0022-328X(02)01174-9,10.1021/ol401727y,10.1055/s-2004-832818,10.1021/jo00109a044,10.1021/ma951840e10.3390/molecules26175390,10.1016/j.mcat.2020.111366,10.1021/acs.macromol.0c00810,10.1002/ijch.202000004,10.1021/jacs.9b11208,10.1021/acs.joc.9b02352,10.1039/c9ob00561g,10.1016/j.tet.2019.02.001,10.1038/s41467-018-07198-7,10.1039/c8nj01518j,10.1039/c8sc00434j,10.1021/acs.orglett.8b00139,10.1002/aoc.4273,10.1021/acs.orglett.8b00235,10.1515/pteridines-2018-0002,10.1246/cl.170897,10.1055/s-0036-1588437,10.1002/aoc.3705,10.1039/c7cc01932g,10.1016/j.polymer.2017.03.036,10.1021/jacs.7b00268,10.1021/acscatal.6b02964,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1016/j.ica.2016.02.004,10.1055/s-0035-1560712,10.1055/s-0034-1378867,10.1055/s-0034-1380424,10.1021/acs.orglett.5b00654,10.1021/ol503560e,10.1039/c5ob01096a,10.1039/c5ra01187f,10.1016/j.jssc.2014.10.002,10.1039/c4dt01856g,10.1002/adsc.201400460,10.1016/j.tet.2014.04.059,10.1021/cr400689s,10.1021/cs4009946,10.1039/c3ob41546e,10.1002/chem.201303637,10.1080/00304948.2013.834772,10.1002/pola.26750,10.1021/ol401727y,10.6023/cjoc201212033,10.1002/aoc.2997,10.1002/aoc.3000,10.1080/00304948.2013.786568,10.1080/00397911.2011.632830,10.1016/j.molstruc.2013.01.008,10.1002/pola.26524,10.1002/pola.26519,10.1002/pola.26320,10.1016/j.tetlet.2012.09.028,10.1021/jo300209d,10.1002/chem.201100967,10.1002/aoc.1804,10.1016/j.tetlet.2010.11.133,10.1021/cr100259t,10.1021/jo101718v,10.1021/jo100846t,10.1016/j.jasms.2010.03.040,10.1055/s-0030-1258116,10.1016/j.tetlet.2010.03.110,10.1002/pola.24046,10.1021/ja910808x,10.1016/j.tetlet.2009.12.028,10.1016/j.tetlet.2009.10.096,10.1002/anie.201005121,10.2174/157017810790534002,10.1021/om900771v,10.1021/ja907882n,10.1021/ol902155e,10.1016/j.jorganchem.2009.04.021,10.1002/ejoc.200900067,10.1021/ol802493z,10.1021/cg8004163,10.1055/s-0028-1087244,10.1021/ma801243x,10.1021/ol801972f,10.1021/ol802049t,10.1021/ja805094j,10.1002/anie.200803814,10.1016/j.catcom.2007.05.008,10.1002/chem.200801008,10.1039/b813605j,10.1021/ol702167t,10.1016/j.tetlet.2007.08.083,10.1021/ma061319s,10.1002/adsc.200700081,10.1016/j.tet.2007.04.016,10.1016/j.tet.2006.11.060,10.1002/chem.200601184,10.1021/ol062314i,10.1016/j.tetlet.2006.01.145,10.1021/jo052369i,10.1021/jo052283p,10.1021/ma049572k,10.1016/j.tet.2005.02.019,10.1055/s-2004-837298,10.1039/b416703a,10.1055/s-2004-832845,10.1055/s-2004-832818,10.1016/j.polymer.2004.05.051,10.1021/ma0355453,10.1002/jlcr.745,10.1021/jo0207473,10.1021/jo020297e,10.1016/S0040-4039(02)01894-4,10.1016/S0022-328X(02)01174-9,10.1021/cr000664r,10.1055/s-2002-22719,10.1021/jo0158377,10.1021/ma0011791,10.1016/S0040-4020(00)01018-8,10.1006/jcat.2000.2865,10.1016/S1387-1609(00)01138-5,10.1246/bcsj.73.985,10.1021/jo991686k,10.1088/0954-0083/11/4/307,10.1016/S0040-4020(99)00788-7,10.1021/jo990805t,10.1021/jo990072c,10.1021/ma9900129,10.1016/S0040-4020(98)00849-7,10.1016/S0040-4039(98)00196-8,10.1021/jo970362y,10.1021/ja964391m,10.1016/S0010-8545(97)90135-1,10.1007/s002890050081,10.1021/jo961464b,10.1246/cl.1997.617,10.1021/ma960557s,10.1016/0032-3861(96)00195-4,10.1021/ma951840e,10.1080/10601329608014921,10.1021/jo00126a047,10.1021/ma00124a005,10.1021/jo00109a044,10.1021/jo00109a045 Long 12/2/2021
295
311FALSEb314246a10.1039/b314246ahttps://sci-hub.wf/10.1039/b314246ahttps://doi.org/10.1039/b314246aNiC-H ActivationWilliamTRUE1091#N/A2004Wang, L
The Sonogashira coupling reaction catalyzed by ultrafine nickel(0) powder
CHEM COMMUN
The Sonogashira coupling reaction catalyzed by ultrafine nickel(0) powder has been developed; terminal alkynes couple with aryl, alkenyl iodide and aryl bromide in the presence of cuprous iodide, triphenylphospbine, potassium hydroxide and ultrafine particle nickel(0) to provide the corresponding cross-coupling products with high yields.
Huaibei Coal Teachers Coll
3/7/2004Csp2_ar-Csp2E-NuXHIHArylVinylKOHIonic-OR_10.1016/j.jorganchem.2021.121703,10.1016/j.tet.2021.132025,10.1039/d1ob00280e,10.1055/s-0040-1705954,10.1021/acs.joc.0c01177,10.3390/catal10020192,10.3390/catal9121019,10.1002/slct.201902018,10.1002/slct.201803144,10.1039/c8nj02486c,10.1002/aoc.3992,10.1016/j.ccr.2017.10.004,10.1007/s11164-017-3079-0,10.1016/j.tet.2017.10.001,10.1016/j.tetlet.2017.06.023,10.1002/ejoc.201700535,10.6023/cjoc201701013,10.1002/ejoc.201700217,10.1039/c6cc09080j,10.1016/j.tetlet.2016.12.011,10.1039/c6ra27910d,10.1007/s10562-016-1880-9,10.1016/j.tetlet.2016.09.049,10.1021/acs.orglett.6b01675,10.1039/c6nj00612d,10.1002/aoc.3492,10.1002/slct.201600113,10.1002/slct.201600051,10.1016/bs.adomc.2016.08.001,10.1039/c6ob00945j,10.1039/c6cc01632d,10.1039/c5ob02558c,10.1002/aoc.3394,10.1016/j.jorganchem.2015.07.029,10.1016/j.tetlet.2015.08.027,10.6023/cjoc201408021,10.1016/j.catcom.2014.11.018,10.1039/c5ob01290b,10.6023/cjoc201408014,10.1039/c5ra22601e,10.1002/cplu.201402169,10.1016/j.tetlet.2014.07.118,10.1016/j.tetlet.2014.03.120,10.1039/c3qi00079f,10.1002/anie.201305326,10.1021/ja408137t,10.1002/aoc.3017,10.1002/adsc.201200876,10.1039/c3dt51674a,10.1021/jo3010183,10.3184/174751912X13379433093990,10.1016/j.tet.2012.03.093,10.1002/cctc.201100358,10.1039/c2ra20119d,10.1055/s-0030-1260138,10.1002/ejoc.201100659,10.1016/j.tet.2011.05.031,10.1002/asia.201000923,10.1055/s-0030-1260023,10.1002/adsc.201000730,10.1055/s-0030-1259542,10.1021/cr100259t,10.1039/c1ob05969f,10.1080/00397911.2010.517363,10.1016/j.molcata.2010.02.010,10.1016/j.tetlet.2009.09.058,10.1002/ejoc.200901084,10.1055/s-0029-1217041,10.1016/j.tetlet.2009.03.146,10.1055/s-0028-1088003,10.1002/adsc.200800517,10.1016/j.tetlet.2008.07.151,10.1002/ejoc.200800394,10.1055/s-2008-1067127,10.1021/ic800499q,10.1055/s-2008-1072615,10.1055/s-2008-1072562,10.1002/anie.200802270,10.1002/chem.200800411,10.1016/j.tet.2007.09.012,10.1021/jo0709448,10.1021/jo070547x,10.1021/jo0623742,10.1021/cr050992x,10.1002/anie.200602761,10.1039/b711884h,10.1016/j.cclet.2006.11.019,10.1080/00397910701227416,10.1055/s-2006-950207,10.1002/cjoc.200690240,10.1055/s-2006-949640,10.1016/j.tetlet.2006.01.118,10.1016/j.molcata.2005.05.046,10.1016/j.tet.2005.07.013,10.1055/s-2005-865233,10.1039/b500952a,10.1002/adsc.200404141,10.1081/SCC-200026232,10.1039/b407090a12/16/2021
296
245FALSEjo00109a04410.1021/jo00109a044https://sci-hub.wf/10.1021/jo00109a044https://doi.org/10.1021/jo00109a044NiC-O ActivationShihongTRUE277421061995Percec, V
ARYL MESYLATES IN METAL-CATALYZED HOMOCOUPLING AND CROSS-COUPLING REACTIONS .1. FUNCTIONAL SYMMETRICAL BIARYLS FROM PHENOLS VIA NICKEL-CATALYZED HOMOCOUPLING OF THEIR MESYLATES
JOURNAL OF ORGANIC CHEMISTRY
Aryl sulfonates including mesylate derived from phenols are converted in high yields to biaryls by homocoupling in the presence of catalytic amounts of zero-valent nickel catalysts generated in situ. This reaction provides the most convenient method for the synthesis of many functional symmetrical biaryls and was applied to the preparation of 2,2'-, 3,3'-, and 4,4'-disubstituted biphenyls and other biaryls. The influence of the electronic and steric effects of substituents attached in the ortho, meta, and para positions of aryl sulfonates and the nature of the sulfonate leaving group on the yield of homocoupled product as well as their influence on the extent of various side reactions were investigated. In addition, the influence of the effects of the polarity and dryness of solvent, halide ion source and concentration, and ratio of catalyst and ligand to aryl sulfonate are discussed.
CASE WESTERN RESERVE UNIV,DEPT MACROMOLEC SCI,WM KECK LABS ORGAN SYNTH,CLEVELAND,OH 44106
2/24/1995Csp2_ar-Csp2_arE-NuOBOTfB(OH)2ArylArylK3PO4Ionic-PO4Weak0.53TM10.1055/s-2004-832818,10.1021/acscatal.9b00744,10.1021/jo7022558,10.1016/S0022-328X(02)01174-9,10.1016/0040-4039(96)01984-3,10.1039/b609064h,10.1021/ol101592r,10.1021/jo2022982,10.1021/jacs.6b11412,10.1021/jo1024464,10.1002/ejoc.201000147,10.1002/adsc.201000710,10.1002/ejoc.201001519,10.1002/ejoc.200900067,10.1021/jo501291y,10.1021/ja903091g,10.1016/S0040-4039(99)00517-1,10.1021/jo202037x,10.1021/acscatal.5b01021,10.1021/jo300547v,10.1246/cl.2005.796,10.1002/anie.200900329,10.1021/jo3001194,10.1021/ma951840e,10.1002/anie.201101461,10.1002/adsc.201100151,10.1002/ejoc.201200444,10.1021/ja038752r,10.1021/jo00126a047,10.1021/jo300209d,10.1021/ja907700e,10.1002/chem.201003403,10.1039/b314246a,10.1021/ol801972f,10.1021/ol401727y,10.1021/jo070912k,10.1002/anie.201102092,10.1021/ol503061c,10.1016/S0040-4020(98)00809-6,10.1021/jacs.1c08502,10.1021/ol016526l,10.1016/j.tetlet.2006.01.14510.1021/acs.orglett.2c00267,10.3390/molecules26237346,10.1021/jacs.1c08502,10.1002/ijch.202100057,10.1039/d1nj03706d,10.1080/00397911.2021.1955931,10.1039/c9cs00571d,10.1002/tcr.202100142,10.1021/acscatal.1c01201,10.1039/d0ra10248b,10.1055/a-1349-3543,10.1002/aoc.6158,10.1039/d0cy01159b,10.1016/j.mcat.2020.111048,10.1039/d0ra04362a,10.1016/j.mcat.2020.110841,10.1021/acs.joc.9b03294,10.3390/catal10030296,10.1002/ijch.202000004,10.1021/acs.organomet.9b00672,10.3390/catal10010136,10.1002/app.48200,10.1080/08927022.2019.1572892,10.1039/c9ob00313d,10.1080/00397911.2019.1584318,10.1021/acscatal.9b00744,10.1016/j.tetlet.2018.12.022,10.1039/c8nj05503c,10.1021/acs.joc.8b02766,10.1002/anie.201809889,10.1002/celc.201800498,10.1016/j.tet.2018.10.025,10.1021/acs.organomet.8b00244,10.1021/acscatal.8b00933,10.1515/pteridines-2018-0002,10.1515/pac-2017-0706,10.1002/ejoc.201701081,10.1021/acs.organomet.7b00446,10.1038/s41570-017-0025,10.1021/jacs.6b11412,10.1021/acscatal.6b02964,10.1002/ejic.201601351,10.1021/acs.joc.6b02093,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.6023/cjoc201512017,10.1016/j.tet.2016.02.069,10.1021/acs.organomet.6b00059,10.1021/acs.inorgchem.5b02936,10.1021/acscatal.5b02021,10.1002/anie.201505699,10.1021/acscatal.5b01021,10.1016/j.jorganchem.2015.04.019,10.1002/cctc.201403057,10.1021/acs.orglett.5b01283,10.3390/molecules20057528,10.1016/j.jorganchem.2015.01.009,10.1021/cs5014927,10.1021/ol503560e,10.1021/ol503061c,10.1016/j.catcom.2014.08.010,10.1002/cplu.201402169,10.1002/ejoc.201402919,10.1007/s11426-014-5138-3,10.1021/jo501291y,10.1002/ejoc.201402120,10.1021/om5001327,10.1016/j.tetlet.2014.02.046,10.1021/cs4009946,10.1016/j.poly.2013.09.041,10.6023/cjoc201307035,10.14233/ajchem.2014.15478,10.1039/c4ra11520a,10.1002/ejoc.201300967,10.14233/ajchem.2013.15232,10.1002/asia.201300688,10.1016/j.jorganchem.2013.05.006,10.1002/pola.26750,10.1021/ol401727y,10.1016/j.tetlet.2013.05.102,10.1016/j.jorganchem.2013.02.029,10.6023/cjoc201212033,10.1016/j.poly.2013.02.059,10.1002/pola.26573,10.1002/pola.26524,10.1002/pola.26519,10.1016/j.tet.2012.12.030,10.1002/cctc.201200417,10.1039/c3cs35521g,10.1002/ejoc.201200914,10.1002/pola.26320,10.1021/om3006036,10.1021/jo301270t,10.1021/jo300547v,10.1002/ejoc.201200444,10.1021/jo300209d,10.1021/jo3001194,10.1021/om201271y,10.1021/ic201849u,10.1021/jo2022982,10.1039/c2dt12187e,10.1039/c2cc15972d,10.1002/anie.201207428,10.1021/jo202037x,10.1002/chem.201100967,10.1002/adsc.201100151,10.1016/j.ica.2011.02.058,10.1021/ar200055y,10.1002/adsc.201100101,10.1002/ejic.201100007,10.1016/j.tetlet.2010.11.133,10.1021/om200060x,10.1021/jo1024464,10.1021/ol200128y,10.1002/chem.201003403,10.1002/ejoc.201001519,10.1021/cr100259t,10.1021/cr1002276,10.1002/adsc.201000710,10.1002/anie.201100293,10.1002/anie.201102092,10.1002/anie.201101461,10.1039/c1cs15114b,10.1039/c1cs15100b,10.1002/chem.201002354,10.1002/chem.201002273,10.1039/c1dt00013f,10.1021/jo101718v,10.1021/ol101592r,10.1021/jo101023t,10.1021/jo100846t,10.1055/s-0030-1258116,10.1016/j.tetlet.2010.03.110,10.1002/ejoc.201000147,10.1016/j.tetlet.2010.01.020,10.1021/ja910808x,10.1016/j.tetlet.2009.10.096,10.1002/anie.201005121,10.1002/ejoc.200901084,10.1021/ja907700e,10.1021/om900771v,10.1021/ja907882n,10.1055/s-0029-1218283,10.1021/ol902155e,10.1021/ja903091g,10.1002/ejoc.200900067,10.1021/jo900098a,10.1021/ol802493z,10.1002/anie.200900329,10.1002/anie.200904033,10.1002/anie.200904306,10.1039/b909341a,10.1021/ol801972f,10.1021/ol802049t,10.1021/jo8014819,10.1002/adsc.200800414,10.1021/ja805094j,10.1016/j.tetlet.2008.07.060,10.1021/ja804672m,10.1021/ol800832n,10.1021/ja711449e,10.1021/jo7022558,10.1002/anie.200704162,10.1002/anie.200802157,10.1002/anie.200803193,10.1039/b803172j,10.1021/jo7019064,10.1016/j.tetlet.2007.08.089,10.1002/adsc.200700081,10.1021/jo070912k,10.1021/jo0709448,10.1016/j.ccr.2007.03.020,10.1016/j.molcata.2007.03.060,10.1021/ja070321b,10.1016/j.tetlet.2007.01.175,10.1002/chem.200600502,10.1002/ejoc.200600469,10.1016/j.tetlet.2006.07.085,10.1055/s-2006-926424,10.1016/j.tetlet.2006.01.145,10.1016/j.tetlet.2006.01.020,10.1021/jo052283p,10.1039/b609064h,10.1021/ol051615+,10.1002/jccs.200500119,10.1246/cl.2005.796,10.1021/ol050608i,10.1021/jo0477897,10.1055/s-2005-864790,10.1016/j.jorganchem.2004.12.022,10.1002/anie.200461444,10.1002/qsar.200420040,10.1055/s-2004-832818,10.1081/SCC-200026232,10.1016/j.polymer.2004.05.051,10.1016/j.ccr.2004.03.025,10.1021/ja038752r,10.1039/b314246a,10.1021/op034104g,10.1021/ja038742q,10.1021/ol036131x,10.2174/0929867033456738,10.1021/om0302948,10.1021/ja036947t,10.1021/jo026449n,10.1021/cc020045r,10.1021/jo020640f,10.1071/CH03113,10.1163/156855503768336289,10.1016/S0040-4020(02)01351-0,10.1016/S0040-4020(02)01188-2,10.1021/ja027190t,10.1016/S0022-328X(02)01174-9,10.1016/S0040-4039(02)00716-5,10.1021/cr000664r,10.1246/bcsj.75.137,10.1021/ol016526l,10.1016/S0040-4020(01)00560-9,10.1021/jo0102157,10.1002/pola.1130.abs,10.1016/S0040-4020(00)00941-8,10.1016/S0040-4020(00)00814-0,10.1016/S0040-4020(00)00815-2,10.1006/jcat.2000.2865,10.1039/b001051k,10.1021/jo991337q,10.1039/a905378f,10.1021/jo990805t,10.1021/jo982135h,10.1016/S0040-4039(99)00517-1,10.1016/S0040-4039(99)00239-7,10.1016/S0022-328X(98)01055-9,10.1016/S0040-4039(98)01882-6,10.1021/jo980704f,10.1016/S0040-4020(98)00809-6,10.1016/S0040-4020(97)10233-2,10.1021/jo9707848,10.1021/jo970439i,10.1002/masy.19971210106,10.1016/S0040-4039(97)00707-7,10.1016/S0010-8545(97)90135-1,10.1007/s002890050081,10.1246/cl.1997.617,10.1016/0040-4039(96)01984-3,10.1021/ma960557s,10.1039/co9960300277,10.1021/ma951840e,10.1016/0040-4039(96)00482-0,10.1002/actp.1996.010470401,10.1080/10601329608014921,10.1021/jo00126a047 Long 12/1/2021
297
313FALSEc5cc01436k10.1039/c5cc01436khttps://sci-hub.wf/10.1039/c5cc01436khttps://doi.org/10.1039/c5cc01436kNiC-H ActivationGerryFALSE1124#N/A2015Shi, BF#N/ANickel-catalyzed direct thiolation of unactivated C(sp(3))-H bonds with disulfides
CHEM COMMUN
The first nickel-catalyzed thiolation of unactivated C(sp(3))-H bonds with disulfides was described. This transformation uses (dppp) NiCl2 as a catalyst and BINOL as a ligand, which are efficient for the thiolation of beta-methyl C(sp(3))-H bonds of a broad range of aliphatic carboxamides. The reaction provides an efficient synthetic pathway to access diverse thioethers.
Zhejiang Univ3/17/2015_xxx10.1002/anie.201510743,10.1039/c6qo00149a,10.1021/acscatal.6b01120,10.1021/acs.orglett.6b0223610.1055/s-0041-1737337,10.1021/acs.chemrev.1c00519,10.1039/d1nj04662d,10.1039/d1sc03667j,10.1002/adsc.202100992,10.1002/adsc.202100816,10.1039/d1cc02517a,10.1002/tcr.202100133,10.1021/acs.organomet.1c00265,10.6023/cjoc202009030,10.1016/j.tetlet.2021.152950,10.1039/d0qo01226b,10.1002/adsc.202000948,10.1002/chem.202003521,10.1055/s-0037-1610756,10.1080/00397911.2020.1761392,10.1002/cjoc.201900468,10.1039/c9qo01497g,10.1246/cl.200015,10.1002/asia.201901757,10.1002/slct.201904651,10.1039/c9sc04169a,10.1016/j.tetlet.2019.151338,10.1021/jacs.9b09109,10.1021/acs.organomet.9b00447,10.1002/tcr.201800093,10.1021/acs.orglett.9b02120,10.1021/acs.orglett.9b02424,10.1016/j.trechm.2019.06.002,10.1002/adsc.201900532,10.1039/c9qo00391f,10.1002/anie.201903511,10.1021/acs.joc.9b00311,10.1002/ajoc.201900199,10.1021/acs.organomet.9b00087,10.1021/acs.organomet.8b00899,10.1002/anie.201900956,10.1039/c8qo01310a,10.1039/c8qo01274a,10.1021/acsomega.9b00030,10.1002/ejoc.201900050,10.1021/acs.chemrev.8b00507,10.1002/ejoc.201801532,10.1039/c8ob02237b,10.1021/acscatal.8b03770,10.1021/jacs.8b07708,10.1039/c8ob01712c,10.1039/c8cs00201k,10.1039/c8ob01481g,10.1021/acs.joc.8b00974,10.1002/adsc.201800090,10.1021/acs.orglett.8b01168,10.1021/acscatal.7b04074,10.1039/c7qo01016h,10.1002/adsc.201701147,10.1039/c7sc04604a,10.1002/ajoc.201700641,10.1002/anie.201703743,10.5059/yukigoseikyokaishi.76.11,10.1016/bs.adomc.2018.02.001,10.1002/adsc.201700949,10.1039/c7cc07086a,10.1002/slct.201701924,10.1039/c7cc05532c,10.1039/c7cc05011a,10.1021/jacs.7b03548,10.1039/c7ob00655a,10.1002/ejoc.201700147,10.1016/j.tet.2017.02.065,10.1002/adsc.201600937,10.1021/acs.organomet.6b00769,10.1021/acs.orglett.6b03856,10.1021/acs.joc.6b02423,10.1016/j.jorganchem.2016.08.025,10.1021/acs.joc.6b01702,10.1002/chem.201602909,10.1021/acs.orglett.6b02236,10.1002/adsc.201600200,10.1002/chem.201603092,10.1021/acs.joc.6b00970,10.1007/s41061-016-0053-z,10.1021/acscatal.6b01120,10.1021/acscatal.6b00964,10.1002/ejoc.201600588,10.1002/adsc.201600156,10.1002/chem.201600293,10.1002/adsc.201600080,10.1021/acs.orglett.6b00494,10.1002/anie.201510743,10.1016/j.tetlet.2016.01.009,10.1002/adsc.201500791,10.1021/acs.joc.5b01943,10.1002/chem.201504179,10.1007/3418_2015_117,10.1039/c6dt02167k,10.1039/c6cc06359d,10.1039/c6qo00149a,10.1039/c6ra04388g,10.1039/c6cc00822d,10.1039/c6qo00156d,10.1039/c6ra18136h,10.6023/A15040278,10.6023/A15040295,10.1002/chem.201502644,10.1021/acs.orglett.5b01634,10.1021/jacs.5b04892,10.1021/acs.orglett.5b01198,10.1039/c5sc02143j,10.1039/c5cc03729h#N/A
298
123FALSEjo00109a04510.1021/jo00109a045https://sci-hub.wf/10.1021/jo00109a045https://doi.org/10.1021/jo00109a045NiC-O ActivationGerryTRUE6081061995Percec, V
ARYL MESYLATES IN METAL-CATALYZED HOMOCOUPLING AND CROSS-COUPLING REACTIONS .2. SUZUKI-TYPE NICKEL-CATALYZED CROSS-COUPLING OF ARYL ARENESULFONATES AND ARYL MESYLATES WITH ARYLBORONIC ACIDS
JOURNAL OF ORGANIC CHEMISTRY
The Ni(O)-catalyzed Suzuki-type cross-coupling reaction of various aryl sulfonates including mesylate with arylboronic acids in the presence of K3PO4 is reported. The Ni(O) catalyst is generated in situ from NiCl2(dppf) and Zn. This novel reaction, which yields unsymmetrical biaryls in good yields under mild conditions, is highly regiospecific and tolerates various functional groups. The influence of the effects of the substituent of the aromatic substrates, the nature of the leaving group, solvent, and type of catalyst, and base on the reaction yield are discussed. The reactivity of various Ni(O) catalysts was compared to that of the less reactive Pd(O) catalysts.
CASE WESTERN RESERVE UNIV,DEPT MACROMOLEC SCI,WM KECK LABS ORGAN SYNTH,CLEVELAND,OH 44106
2/24/1995Csp2_ar-Csp2_arE-EOOOMsOMsArylArylNitrogenNitrogen(charged)Weak0.36_10.1021/jo00126a047,10.1021/jo049940i,10.1021/ol401727y,10.1016/j.tetlet.2006.01.145,10.1002/adsc.201400460,10.1021/ol801972f,10.1021/ma951840e,10.1055/s-2004-83281810.1021/acs.orglett.8b02526,10.1002/aoc.4273,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1021/acs.orglett.5b02115,10.1021/acs.orglett.5b01283,10.1002/adsc.201400460,10.1021/cr400689s,10.1002/pola.26750,10.1021/ol401727y,10.1002/pola.26524,10.1002/pola.26519,10.1016/j.tetlet.2013.01.040,10.1021/cr100259t,10.1021/jo101718v,10.1021/jo101023t,10.1055/s-0030-1258116,10.1021/ja910808x,10.1016/j.tetlet.2009.10.096,10.1021/om900771v,10.1021/ja907882n,10.1055/s-0029-1218283,10.1021/ol902155e,10.1016/j.tet.2009.02.040,10.1021/ol802493z,10.1021/ma802215y,10.1021/ol801972f,10.1021/jo8014819,10.1021/ol800977n,10.1021/ja711449e,10.1002/anie.200802157,10.1002/anie.200803193,10.1021/ja073714j,10.1016/j.tetlet.2006.01.145,10.1039/b612235c,10.1055/s-2004-832818,10.1016/j.polymer.2004.06.009,10.1021/jo049940i,10.1016/S1010-6030(03)00113-8,10.1023/A:1022529227102,10.1016/S0040-4020(00)01018-8,10.1039/a905378f,10.1021/jo990805t,10.1016/S0022-328X(98)01055-9,10.1016/S0010-8545(97)90135-1,10.1007/s002890050081,10.1246/cl.1997.617,10.1016/S0040-4039(96)02065-5,10.1021/ma960557s,10.1021/ma951840e,10.1080/10601329608014921,10.1021/jo00126a047,10.1021/ma00124a005checked by Kelly1/20/2022
299
238FALSEjo00126a04710.1021/jo00126a047https://sci-hub.wf/10.1021/jo00126a047https://doi.org/10.1021/jo00126a047NiC-O ActivationLongTRUE227121061995Percec, V
ARYL MESYLATES IN METAL-CATALYZED HOMOCOUPLING AND CROSS-COUPLING REACTIONS .3. A SIMPLE AND GENERAL-METHOD FOR THE SYNTHESIS OF 2,2'-DIAROYL-4,4'-DIHYDROXYBIPHENYLS
JOURNAL OF ORGANIC CHEMISTRY
CASE WESTERN RESERVE UNIV,DEPT MACROMOLEC SCI,W M KECK LABS ORGAN SYNTH,CLEVELAND,OH 44106
10/20/1995Csp2_ar-Csp3E-NuOMgOMsMgXArylAlkylNo baseNo BaseWeak0.36_10.1021/acscatal.7b02618,10.1002/anie.200803814,10.1021/acscatal.9b00744,10.1021/acs.orglett.6b02265,10.1021/jo300209d,10.1038/ncomms12937,10.1039/b803072c,10.1021/ol801972f,10.1021/ma951840e,10.1021/acs.joc.8b02498,10.1021/acscatal.1c04800,10.1016/S0022-328X(02)01174-910.1021/acscatal.1c04800,10.3390/molecules26175390,10.1002/chem.202101906,10.1063/5.0038672,10.1016/j.mcat.2020.111366,10.1055/s-0040-1705943,10.1007/s10870-020-00859-w,10.1002/ajoc.202000334,10.1248/cpb.c20-00196,10.1055/s-0040-1707131,10.1021/acs.chemrev.9b00682,10.1007/s41981-020-00094-6,10.1134/S1070363220040258,10.1002/ijch.202000004,10.1021/acscatal.9b04586,10.1016/j.poly.2019.114269,10.1002/aoc.5385,10.1021/acscatal.9b00744,10.1016/j.jorganchem.2019.01.017,10.1002/aoc.4691,10.1016/j.poly.2018.11.004,10.1021/acs.orglett.8b03476,10.1016/j.tet.2018.10.025,10.1021/acs.joc.8b02498,10.1002/adsc.201800343,10.1007/s41061-018-0203-6,10.1016/j.tetlet.2018.02.043,10.1039/c8ob00238j,10.1515/pteridines-2018-0002,10.1002/slct.201702614,10.1016/j.tetlet.2017.10.041,10.1055/s-0036-1588508,10.1007/s10904-017-0636-3,10.1021/acscatal.7b02618,10.1021/acs.joc.7b01653,10.3762/bjoc.13.174,10.1016/j.tet.2017.05.088,10.1002/slct.201700684,10.1002/ejic.201700057,10.1021/acs.orglett.7b00732,10.1021/acs.joc.6b02865,10.1002/slct.201601809,10.1039/c7ra04817c,10.1016/j.jcou.2016.10.013,10.1016/j.catcom.2016.07.019,10.1002/jhet.2513,10.1055/s-0035-1561673,10.1021/acs.orglett.6b02265,10.1038/ncomms12937,10.1055/s-0035-1562499,10.1055/s-0035-1562342,10.1016/j.jorganchem.2016.04.034,10.1055/s-0035-1561408,10.1016/j.tet.2016.02.069,10.1039/c6ra12557c,10.1039/c6nj01434h,10.1071/CH15496,10.1039/c6dt00064a,10.1016/j.tetlet.2015.10.014,10.1021/acs.joc.5b01248,10.1016/j.tetlet.2015.06.087,10.1002/adsc.201500304,10.1002/chem.201500058,10.1016/j.molcata.2015.03.002,10.1002/ejoc.201500156,10.1055/s-0034-1379878,10.1016/j.jcou.2014.11.002,10.1039/c5ob01874a,10.1039/c5nj00867k,10.1039/c5ra03869c,10.1039/c4gc02047b,10.1055/s-0034-1379206,10.1039/c4cc08367a,10.1055/s-0034-1379483,10.1002/chem.201404705,10.1007/s10562-014-1345-y,10.1002/ajoc.201402154,10.1021/ja505576g,10.1002/ajoc.201402084,10.1002/aoc.3191,10.1002/jccs.201400027,10.1016/j.molcata.2014.02.006,10.1002/cjoc.201300830,10.1002/asia.201301500,10.1021/ol500112y,10.1016/j.tetlet.2014.01.001,10.1039/c4ra09450f,10.1055/s-0033-1339918,10.1002/chem.201302999,10.1055/s-0033-1339666,10.1021/om400784w,10.1016/j.molcata.2013.05.012,10.1002/aoc.3014,10.1002/pola.26750,10.1002/ejoc.201300248,10.1002/asia.201300045,10.1021/ie3035338,10.1055/s-0032-1318482,10.1002/pola.26524,10.1002/pola.26519,10.1002/cjoc.201200711,10.1039/c3ra44884c,10.2174/157017812803901854,10.1021/jo302088t,10.1002/aoc.2871,10.1016/j.tetlet.2012.06.054,10.1021/jo3008397,10.1021/jo300209d,10.1002/ejoc.201101773,10.1039/c2cc32676k,10.1039/c2ob25225b,10.1039/c2cc17283f,10.1039/c2ob06795a,10.1002/ejoc.201101121,10.1021/ol2020863,10.1007/s11243-011-9525-8,10.1016/j.tetlet.2011.04.078,10.1016/j.tetlet.2010.11.133,10.3724/SP.J.1088.2011.01018,10.1002/ejoc.201001667,10.1021/cr100259t,10.1021/cr100347k,10.1021/cr100346g,10.1002/adsc.201000747,10.1021/ol102784c,10.1016/j.bmcl.2010.12.020,10.1039/c1ra00406a,10.1039/c1cc11603g,10.1002/chem.201002273,10.3390/molecules16010590,10.1039/c0ob00639d,10.1039/c1ob05597f,10.1055/s-0030-1259079,10.1021/om100816d,10.1021/ar100082d,10.1021/jo101718v,10.1021/ol1018739,10.1055/s-0030-1258545,10.1021/jo101023t,10.1002/adsc.201000223,10.1055/s-0030-1258116,10.1021/cr9000786,10.1021/ja910808x,10.1016/j.tetlet.2009.11.025,10.1016/j.tetlet.2009.10.096,10.1002/adsc.200900671,10.1007/978-3-642-12073-2_3,10.1039/b918117b,10.1021/jo902185c,10.1021/om900771v,10.1021/ja907882n,10.1021/ol902155e,10.1002/adsc.200900501,10.1021/jo900385d,10.1021/jo802731j,10.1021/ol900009a,10.1021/jo8024253,10.1016/j.tet.2008.11.062,10.1016/j.tetlet.2008.11.082,10.1021/ol802493z,10.1039/b907362k,10.1039/b820790a,10.1021/ol801972f,10.1021/ol802049t,10.1021/jo8014819,10.1021/ja711449e,10.1016/j.tetlet.2007.12.118,10.1002/ejoc.200700978,10.1002/anie.200802157,10.1002/anie.200803193,10.1002/anie.200803814,10.1071/CH08095,10.1039/b803072c,10.3184/030823408X283711,10.1080/00397910701831498,10.1021/ol071248x,10.1016/j.ccr.2007.03.020,10.1002/ejoc.200700098,10.1002/anie.200701282,10.1002/chem.200601737,10.1080/00397910701490212,10.1021/ol062344l,10.1021/op060083p,10.1016/j.tetlet.2006.07.008,10.1016/j.tetlet.2006.03.101,10.1351/pac200678020377,10.1039/b605732b,10.1021/jo051394l,10.1021/ol051615+,10.1016/j.tet.2005.03.078,10.1016/j.polymer.2004.05.051,10.1021/jo0350561,10.1021/jo026449n,10.1021/ja0299708,10.3998/ark.5550190.0004.608,10.1039/b305617a,10.1016/S0022-328X(02)01174-9,10.1006/jcat.2000.2865,10.1135/cccc20000729,10.1016/S0040-4020(99)00756-5,10.1039/a906086c,10.1021/jo990805t,10.1016/S0040-4039(99)01178-8,10.1039/a705078j,10.1021/jo960058p,10.1016/S0010-8545(97)90135-1,10.1007/s002890050081,10.1246/cl.1997.617,10.1021/ma960557s,10.1021/ma951840e,10.1080/10601329608014921Kelly12/2/2021
300
316FALSEacscatal.6b0079310.1021/acscatal.6b00793https://sci-hub.wf/10.1021/acscatal.6b00793https://doi.org/10.1021/acscatal.6b00793NiC-N ActivationLongTRUE2515542016Garg, NK
Nickel-Catalyzed Alkylation of Amide DerivativesACS CATAL
We report the catalytic alkylation of amide derivatives, which relies on the use of nonprecious metal catalysis. Amide derivatives are treated with organozinc reagents, utilizing nickel catalysis, to yield ketone products. The methodology is performed at ambient temperature and is tolerant of variation in both coupling partners. A precursor to a nanomolar glucagon receptor modulator was synthesized using the methodology, underscoring the mild nature of this chemistry and its potential utility in pharmaceutical synthesis. These studies are expected to further promote the use of amides as synthetic building blocks.
Univ Calif Los Angeles
5/1/2016TRUETRUEFALSECsp2-Csp3-ring(s)E-NuNZn
N(Me)Tos
ZnX
Carbonyl
BenzylNo baseNo Base_x10.1021/acs.orglett.7b00831,10.1039/c7sc01980g,10.1021/acscatal.7b01444,10.1021/jacs.9b00111,10.1021/jacs.7b12865,10.1021/jacs.7b02389,10.1021/jacs.7b06191,10.1002/anie.201607856,10.1021/acs.orglett.8b01021,10.1002/anie.202103327,10.1055/s-0036-1588845,10.1002/chem.201605095,10.1021/acscatal.7b03688,10.1021/acs.orglett.6b02952,10.1002/chem.20170286710.1002/anie.202201142,10.1021/acscatal.1c05738,10.1039/d1ob02414k,10.1039/d1ob02349g,10.1002/anie.202114731,10.1039/d1qo01219c,10.1038/s42004-021-00575-2,10.1039/d1ob01409a,10.1007/s11426-021-1035-5,10.1039/d1sc02266k,10.1002/anie.202103327,10.1021/acs.orglett.0c03260,10.1055/s-0040-1707133,10.1016/j.tetlet.2020.152444,10.1021/acscatal.0c03334,10.1055/s-0040-1707301,10.1039/d0qo00797h,10.1016/j.trechm.2020.08.001,10.1002/anie.202004441,10.1021/acs.orglett.0c00885,10.1021/acs.orglett.0c00442,10.1002/asia.202000117,10.1021/jacs.9b11944,10.1021/acs.joc.9b02826,10.1021/acs.orglett.9b03434,10.1002/ejoc.201901396,10.1177/1747519819873514,10.1039/c9cc05763c,10.1021/acs.joc.9b01699,10.1021/acs.orglett.9b02513,10.1055/s-0037-1611549,10.1002/ejoc.201900531,10.1039/c9nj01748h,10.1039/c9qo00106a,10.1021/acs.joc.9b00669,10.1016/j.tetlet.2019.04.004,10.1002/adsc.201801577,10.1021/acs.jchemed.8b00489,10.1002/chem.201802635,10.1021/jacs.9b00111,10.1021/acs.organomet.8b00720,10.1002/cctc.201801098,10.1002/asia.201801317,10.1002/ejoc.201801124,10.1039/c8cs00335a,10.1021/acs.orglett.8b02911,10.1039/c8qo00591e,10.3390/molecules23102681,10.3390/molecules23102412,10.1142/S1793292018500741,10.1021/acscatal.8b01380,10.1002/ejoc.201800109,10.1016/j.tetlet.2018.05.003,10.1021/acs.orglett.8b01021,10.1021/acs.joc.8b00160,10.1021/acs.orglett.8b00949,10.1016/j.cattod.2017.09.006,10.1016/j.tetlet.2018.01.097,10.1021/jacs.7b12865,10.1002/chem.201800336,10.1021/acscatal.7b03688,10.1055/s-0036-1590932,10.1021/acscatal.7b02599,10.1080/10426507.2017.1415899,10.1021/acs.orglett.7b03191,10.1021/jacs.7b09482,10.1007/s11426-017-9025-1,10.1039/c7cs00182g,10.1021/acs.orglett.7b02877,10.1002/chem.201702867,10.1021/acs.orglett.7b02096,10.1039/c7sc02692g,10.1039/c7sc01980g,10.1021/jacs.7b06191,10.1055/s-0036-1588845,10.1002/chem.201702608,10.1021/acs.orglett.7b01575,10.1039/c7sc01170a,10.1021/acscatal.7b01444,10.1021/acs.orglett.7b01194,10.1021/acs.orglett.7b01199,10.1021/acs.joc.7b00570,10.1002/anie.201703174,10.1002/chem.201605012,10.1021/acs.orglett.7b00831,10.1021/acs.orglett.7b00989,10.1038/ncomms14993,10.1021/acs.orglett.7b00796,10.1021/jacs.7b02389,10.1021/acs.orglett.7b00429,10.1021/acs.orglett.7b00683,10.1002/anie.201612624,10.1021/acs.orglett.7b00373,10.1021/acscatal.6b03616,10.1039/c7ob00086c,10.1021/acs.organomet.6b00769,10.1021/acscatal.6b03277,10.1021/jacs.6b12329,10.1021/acs.joc.6b02666,10.1021/acscatal.6b03040,10.1002/chem.201605095,10.1021/acs.orglett.6b03345,10.1021/acs.joc.6b02093,10.1021/acs.joc.6b02294,10.1002/adsc.201600555,10.1002/anie.201607856,10.1021/acs.orglett.6b02952,10.1021/acscatal.6b02323,10.1007/s10876-016-1059-y,10.1055/s-0036-1588080,10.1002/chem.201604061,10.1002/chem.201603543,10.1021/acs.orglett.6b01836,10.1021/acs.orglett.6b01758,10.1039/c6cc06428k11/1/2021MAY2016FALSEFALSEFALSEFALSE653176
301
204FALSEs-2000-628710.1055/s-2000-6287https://sci-hub.wf/10.1055/s-2000-6287https://doi.org/10.1055/s-2000-6287NiC-O ActivationGerryTRUEx721#N/A2000Rudolph, J
Catalytic Coupling of Aryl Sulfonates with sp2-Hybridized Nitrogen Nucleophiles: Palladium- and Nickel-catalyzed Synthesis of N-Aryl SulfoximinesSYNTHESIS
Several sulfoximines have been arylated in good to high yield by palladium catalysis using aryl nonaflates and aryl triflates. Moreover, the successful synthesis of N-aryl sulfoximines from aryl tosylates is described using a Ni(COD)2/BINAP catalyst.

#N/A2/16/2000Csp2_ar-Nsp2E-NuOHOTfHAryl
thionitrosyl
Cs2CO3Ionic-CO3Weak0.53_cannot find in web of sciencewos not available1/3/2022
302
91FALSEjo00205a04210.1021/jo00205a042https://sci-hub.wf/10.1021/jo00205a042https://doi.org/10.1021/jo00205a042NiC-O ActivationGerryTRUE471691985WENKERT, E
ARYL MESYLATES IN METAL-CATALYZED HOMO-COUPLING AND CROSS-COUPLING REACTIONS .4. SCOPE AND LIMITATIONS OF ARYL MESYLATES IN NICKEL-CATALYZED CROSS-COUPLING REACTIONS
JOURNAL OF ORGANIC CHEMISTRY
This paper describes the synthetic utility of aryl mesylates derived from phenols in various transition metal-catalyzed cross-coupling reactions. The Ni(0)-catalyzed cross-couplings of aryl mesylates with organometallic carbanion synthons (organotin, -magnesium, and -zinc compounds) are described. It is demonstrated that Stille-type coupling reaction based on organotin compounds results in low yields due to the sluggish transmetalation step of the reaction cycle. Good to high yields of cross-coupled products are obtained by using more reactive organomagnesium and -zinc compounds as coupling partners. The Ni(0)-catalyzed cyanation of aryl mesylates is also described. Various aryl mesylates are converted to aryl nitriles in high yields by reaction with KCN in the presence of Ni(0) catalyst in DMF. In addition, the Ni(0)-catalyzed aromatic nucleophilic substitution reaction of aryl mesylates with the heteroatom-nucleophile, benzenethiolate anion, is also presented.
UNIV CALIF SAN DIEGO,DEPT CHEM D006,LA JOLLA,CA 92093
3/1/1985Csp3-Csp3E-NuOMg
O(Ring-Opening)
MgXAlkylAlkylNo baseNo BaseWeak1_10.1021/jo00106a03110.1021/acs.jafc.0c04131,10.1055/s-0037-1611537,10.1186/s12915-017-0427-x,10.1021/acs.orglett.6b02977,10.1039/c5nj01354b,10.1007/3418_2012_42,10.1590/S0100-40422012001100039,10.1038/nn.2800,10.1002/chem.201002273,10.1002/adsc.201000350,10.1039/b920285d,10.1016/j.tet.2007.09.074,10.1055/s-2006-939051,10.1002/anie.200462672,10.1021/la010473z,10.1016/S0040-4020(99)00425-1,10.1021/jo962307f,10.1021/jo00057a055,10.1039/p19920003419,10.1021/jo00042a046,10.1016/S0040-4020(01)88230-2,10.1016/0022-328X(92)83346-J,10.1135/cccc19911916,10.1135/cccc19911744,10.1021/jo00304a032,10.1080/00304949009356683,10.1016/0040-4039(90)80134-8,10.1080/07328308908048004,10.1016/S0040-4020(01)89243-7,10.1246/bcsj.61.3368,10.1016/S0040-4039(00)86058-X,10.1016/0040-4039(88)85233-X,10.1246/nikkashi.1987.1227,10.1039/c39870000429,10.1016/S0040-4039(01)81055-81/25/2022
303
171FALSEjo010452+10.1021/jo010452+https://sci-hub.wf/10.1021/jo010452+https://doi.org/10.1021/jo010452+NiC-O ActivationLongTRUE896582001Yang, Z
SYNTHESIS OF ACYCLIC, CIS OLEFINIC PHEROMONES BY WAY OF NICKEL-CATALYZED GRIGNARD REACTIONS
JOURNAL OF ORGANIC CHEMISTRY
Harvard Univ11/16/2001Csp2_ar-Csp2E-NuOZn
OP(O)(OEt)2
ZnXArylVinylK3PO4Ionic-PO4Strong0.04_10.1021/ol9028308,10.1021/acscatal.7b04030,10.1002/adsc.201100151,10.1055/s-2004-832818,10.1002/adsc.200404150,10.1021/jo070912k10.1021/acscatal.1c01077,10.1016/j.tetlet.2019.151057,10.1007/s10600-019-02705-8,10.3390/molecules23102417,10.1002/jhet.3280,10.1016/j.tetlet.2018.05.032,10.6023/cjoc201708058,10.1021/acscatal.7b04030,10.1002/bkcs.10819,10.1002/bkcs.10777,10.1002/anie.201506437,10.1055/s-0035-1560175,10.1016/j.tetlet.2015.10.009,10.1016/j.tetlet.2015.07.033,10.1002/ejoc.201500610,10.1002/ajoc.201500044,10.1016/j.tet.2014.07.059,10.1016/j.tetlet.2014.01.148,10.1016/j.tet.2013.10.089,10.1016/j.tet.2012.12.030,10.1039/c3ra23188g,10.1016/j.tetasy.2012.09.012,10.1007/s10593-012-1083-2,10.1021/jo301086k,10.1016/j.tet.2012.05.021,10.1016/j.tetlet.2012.03.108,10.1055/s-0031-1289717,10.1002/adsc.201100646,10.1021/jo202577m,10.3184/174751912X13249848731931,10.1039/c2cc18150a,10.1002/chem.201103304,10.1039/c2cc34551j,10.1002/adsc.201100151,10.1021/ol2012132,10.1016/j.tetlet.2011.03.151,10.1021/cr100259t,10.1021/cr100327p,10.1039/c1cs15100b,10.1002/chem.201002273,10.1055/s-0030-1259104,10.1021/ol1020477,10.1002/ejoc.201000134,10.1021/ol9028308,10.1002/anie.201001799,10.1080/10426500903036022,10.1016/j.tet.2009.06.089,10.1002/adsc.200900287,10.1021/jo900098a,10.1021/jo900291f,10.1021/ol802239n,10.1039/b801888j,10.1021/ol702167t,10.1021/jo071117+,10.1021/jo070912k,10.1021/cc070030z,10.1021/jo070528n,10.1021/ja070321b,10.1002/adsc.200600527,10.1002/ejoc.200600469,10.1016/j.tetlet.2006.07.085,10.1021/jo0607360,10.1002/anie.200600442,10.1039/b600540c,10.1080/00397910600638937,10.1080/00397910600773692,10.1055/s-2005-921920,10.1016/j.tetlet.2005.08.136,10.1021/ol051871m,10.1021/jo050671l,10.1016/j.tetlet.2005.03.203,10.1002/adsc.200404297,10.1002/adsc.200404150,10.1055/s-2004-832818,10.1021/cr020101a,10.1039/b411111g,10.1016/S0010-8545(03)00123-1,10.1016/S0040-4039(03)00873-6,10.1351/pac200375040421,10.1016/S0040-4039(02)01600-3,10.1021/ol020159bKelly12/2/2021
304
321FALSEanie.20160785610.1002/anie.201607856https://sci-hub.wf/10.1002/anie.201607856https://doi.org/10.1002/anie.201607856NiC-N ActivationKellyTRUE12213542016Garg, NK
Nickel-Catalyzed Esterification of Aliphatic Amides
ANGEW CHEM INT EDIT
Recent studies have demonstrated that amides can be used in nickel-catalyzed reactions that lead to cleavage of the amide C-N bond, with formation of a C-C or C-heteroatom bond. However, the general scope of these methodologies has been restricted to amides where the Carbonyl is directly attached to an arene or heteroarene. We now report the nickel-catalyzed esterification of amides derived from aliphatic carboxylic acids. The transformation requires only a slight excess of the alcohol nucleophile and is tolerant of heterocycles, substrates with epimerizable stereocenters, and sterically congested coupling partners. Moreover, a series of amide competition experiments establish selectivity principles that will aid future synthetic design. These studies overcome a critical limitation of current Ni-catalyzed amide couplings and are expected to further stimulate the use of amides as synthetic building blocks in C-N bond cleavage processes.
Univ Calif Los Angeles
11/21/2016TRUETRUEFALSECsp2-Osp2E-NuNH
N(Bn)Boc
H
Carbonyl
ORNo baseNo Base_x10.1021/acscatal.7b00442,10.1039/c7sc01980g,10.1021/acscatal.7b01444,10.1021/jacs.9b00111,10.1021/jacs.7b02389,10.1002/anie.202103327,10.1021/acs.orglett.9b04497,10.1021/acscatal.7b03688,10.1055/s-0036-1588845,10.1002/anie.201808560,10.1021/acs.orglett.8b01021,10.1002/chem.201702867,10.1021/acs.orglett.7b0083110.1002/slct.202104272,10.1021/acscatal.1c05738,10.1002/jlcr.3962,10.1016/j.poly.2021.115628,10.1039/d1ob02349g,10.3389/fchem.2021.822625,10.1002/chem.202102734,10.1002/bkcs.12371,10.1002/ejoc.202100645,10.1002/ejoc.202100478,10.1002/anie.202103327,10.1002/chem.202100390,10.1021/acs.orglett.0c04300,10.1021/acssuschemeng.0c08262,10.1002/chem.202003752,10.1039/d0sc05137c,10.1021/acs.orglett.0c03260,10.1007/s11426-020-9883-3,10.1002/adsc.202000794,10.1016/j.tetlet.2020.152444,10.1021/acscatal.0c03334,10.1039/d0qo00797h,10.1016/j.trechm.2020.08.001,10.1021/acs.organomet.0c00485,10.1039/d0qo00713g,10.1021/acs.orglett.0c02457,10.1002/chem.202001447,10.1002/cctc.201902290,10.1002/aoc.5626,10.1021/acscatal.9b05074,10.1021/acs.orglett.0c00885,10.1021/acs.orglett.0c00485,10.1007/s11426-019-9665-5,10.1038/s41467-020-14799-8,10.1021/acs.orglett.9b04497,10.1021/acs.joc.9b02826,10.1021/acs.orglett.9b03434,10.1038/s41929-019-0407-3,10.1038/s41929-019-0392-6,10.1055/s-0039-1690178,10.1177/1747519819873514,10.1021/acs.orglett.9b03274,10.1002/ejoc.201901291,10.1021/acs.joc.9b02299,10.1002/adsc.201900819,10.1039/c9cc05763c,10.1002/tcr.201900044,10.1021/acs.joc.9b01103,10.1021/acs.orglett.9b02513,10.1002/adsc.201900485,10.1002/chem.201901446,10.1002/ejoc.201900531,10.1039/c9nj01748h,10.1039/c9qo00106a,10.1002/cctc.201900254,10.1016/j.ccr.2019.01.005,10.1021/acs.jchemed.8b00489,10.1021/acs.oprd.8b00424,10.3390/molecules24071234,10.1039/c8sc05819a,10.1002/chem.201802635,10.1021/jacs.9b00111,10.1055/s-0037-1610664,10.1038/s41467-019-08413-9,10.1021/acs.organomet.8b00720,10.1002/asia.201801317,10.1038/s41929-018-0220-4,10.1021/acs.orglett.8b03304,10.1039/c8cs00335a,10.1039/c8qo00591e,10.3390/molecules23102681,10.3390/molecules23102412,10.1002/anie.201808560,10.1021/acs.orglett.8b02323,10.1021/acs.orglett.8b01896,10.1002/ajoc.201800421,10.1021/acs.oprd.8b00182,10.1016/j.tetlet.2018.05.003,10.1021/acs.orglett.8b01021,10.1021/acs.joc.8b00160,10.1021/acs.orglett.8b00949,10.1016/j.tetlet.2018.01.097,10.1002/chem.201800336,10.1039/c7gc03534a,10.1021/acscatal.7b03688,10.1055/s-0036-1590932,10.1021/acscatal.7b02599,10.1039/c7ra12152k,10.1039/c7ob02269g,10.1021/jacs.7b09482,10.1007/s11426-017-9025-1,10.1039/c7cs00182g,10.1002/ejoc.201700748,10.1002/chem.201702867,10.1039/c7sc02692g,10.1039/c7sc01980g,10.1002/anie.201703667,10.1055/s-0036-1588845,10.1002/chem.201702608,10.1021/acs.orglett.7b01575,10.1021/acs.joc.7b00749,10.1021/acscatal.7b01444,10.1016/j.tet.2017.03.073,10.1021/acs.orglett.7b01194,10.1021/acs.joc.7b00971,10.1021/acs.orglett.7b01199,10.1002/anie.201703174,10.1002/chem.201605012,10.1021/acs.orglett.7b00831,10.1038/ncomms14993,10.1021/acscatal.7b00442,10.1021/acs.orglett.7b00796,10.1021/jacs.7b02389,10.1021/acs.orglett.7b00429,10.1021/acs.orglett.7b00683,10.1021/acs.orglett.7b00373,10.1021/acscatal.6b03616,10.1039/c7ob00086c,10.1021/acscatal.6b0327711/1/2021NOV 212016FALSEFALSEFALSEFALSE554815129
305
280FALSEjo015837710.1021/jo0158377https://sci-hub.wf/10.1021/jo0158377https://doi.org/10.1021/jo0158377NiC-O ActivationShihong21-MarTRUE36132001Leadbeater, NE
Nickel-catalyzed cross-couplings of 4-diethylphosphonooxycoumarins with organozinc reagents: An efficient new methodology for the synthesis of 4-substituted coumarins
JOURNAL OF ORGANIC CHEMISTRY
11/2/2001Csp3-Csp1E-NuOHOAcHAllylAlkyneNo baseNo BaseMedium0.3110.1021/acs.joc.1c00577,10.1039/d1qo00309g,10.3390/catal10040372,10.1021/acs.orglett.0c00108,10.1007/s11051-019-4533-2,10.1515/pac-2017-0706,10.1002/slct.201702278,10.1021/jacs.7b06338,10.1016/j.ica.2016.10.001,10.1039/c5cc10518h,10.1002/ejoc.201500522,10.1021/acs.joc.5b00728,10.1515/pac-2014-1108,10.1021/jo501886w,10.1016/j.ceramint.2013.12.017,10.1021/ja406025p,10.1016/j.tetlet.2012.10.005,10.1021/cr100259t,10.1021/om1003732,10.1166/jnn.2010.2343,10.1016/j.tetlet.2009.04.012,10.1002/aoc.1480,10.1002/aoc.1367,10.1166/jnn.2007.084,10.1021/jo0709448,10.1021/ic0606227,10.1166/jnn.2006.017,10.1055/s-2006-926305,10.1021/om049455d,10.1016/S0010-8545(03)00123-1,10.1016/S0040-4039(02)02643-6,10.1135/cccc20030917,10.1016/S0010-8545(02)00201-1,10.1016/S0040-4039(01)02221-3,10.1135/cccc200212233/24/2022
306
309FALSEjo026449n10.1021/jo026449nhttps://sci-hub.wf/10.1021/jo026449nhttps://doi.org/10.1021/jo026449nNiC-O ActivationWilliam23-JunTRUE651#N/A2003Park, K
Bis-cyclopentadienyl nickel (nickelocene): A convenient starting material for reactions catalyzed by Ni(0) phosphine complexes
JOURNAL OF ORGANIC CHEMISTRY
3/21/2003Csp3-Csp2_arE-NuOMg
OSO2Ph
MgXAlkylArylNo baseNo BaseWeak0.77/6/2022
307
324FALSEc3988000097510.1039/c39880000975https://sci-hub.wf/10.1039/c39880000975https://doi.org/10.1039/c39880000975NiC-N ActivationKellyTRUE12115691988WENKERT, E
NICKEL-INDUCED CONVERSION OF CARBON NITROGEN INTO CARBON CARBON BONDS - ONE-STEP TRANSFORMATIONS OF ARYL, QUATERNARY AMMONIUM-SALTS INTO ALKYLARENES AND BIARYLS
J CHEM SOC CHEM COMM
UNIV CALIF SAN DIEGO,DEPT CHEM,D-006,LA JOLLA,CA 92093
7/15/1988FALSEFALSEFALSECsp2_ar-Csp2_arE-NuNMg
NMe3+I-
MgXArylArylEt3NNitrogenNitrogen(neutral)E-H_x10.1038/ncomms12937,10.1002/anie.201100683,10.1021/acscatal.7b01058,10.1021/ja034908b,10.1039/c3ob41989d,10.1039/c4qo00321g,10.1021/jo300209d,10.1021/acs.orglett.9b00242,10.1039/c2dt30886j,10.1002/anie.201511197,10.1016/j.tet.2017.06.004,10.1021/om500452c,10.1002/chem.201603436,10.1002/ajoc.201700569,10.1021/ja505823s10.1177/17475198211063806,10.3390/molecules26195947,10.1016/j.tet.2021.132431,10.1039/d1ob01468d,10.1021/acs.joc.1c01339,10.1039/c9cs00571d,10.1039/d1qo00759a,10.1134/S1070428021060117,10.1039/d1cc01734a,10.1055/a-1482-2567,10.1039/d1sc00757b,10.1039/d1gc00141h,10.1016/j.mcat.2021.111500,10.1021/acs.joc.0c02992,10.1021/acs.orglett.0c03660,10.1055/s-0040-1705986,10.1021/acscatal.0c03341,10.1021/acscatal.0c03334,10.1021/acs.joc.0c01274,10.1248/cpb.c20-00196,10.1016/j.catcom.2020.106009,10.1016/j.tetlet.2020.151975,10.1039/d0qo00173b,10.1021/acs.orglett.0c00736,10.1002/chem.202000412,10.1039/c9ob02667c,10.1002/ajoc.201900759,10.1039/c9ob02107h,10.1039/c9qo01033e,10.1021/acs.joc.9b01877,10.1021/acs.orglett.9b02820,10.1021/acscatal.9b02440,10.1016/j.tet.2019.07.007,10.1021/acs.oprd.9b00194,10.1016/j.isci.2019.04.038,10.1039/c9sc01083a,10.1002/chem.201900886,10.1021/acscatal.9b00218,10.1021/acs.orglett.9b00242,10.1021/acs.joc.8b02150,10.1039/c8cc07093h,10.6023/cjoc201803013,10.1002/anie.201806271,10.1002/anie.201804628,10.1039/c8cc03760d,10.1021/acs.joc.8b00965,10.1039/c8ob00488a,10.6023/cjoc201710034,10.1038/s41467-018-03928-z,10.1002/anie.201712618,10.1002/ajoc.201700569,10.1039/c7qo00731k,10.1002/asia.201701342,10.1039/c7gc02775c,10.1002/ijch.201700044,10.1021/jacs.7b08579,10.1002/asia.201701132,10.1016/j.tet.2017.06.004,10.1002/asia.201700313,10.1039/c7qo00174f,10.1021/jacs.7b05273,10.1021/acscatal.7b01058,10.6023/cjoc201612014,10.1039/c6sc05705e,10.1016/j.tet.2016.10.018,10.1002/chem.201603436,10.1038/ncomms12937,10.6023/cjoc201510031,10.1002/anie.201600697,10.1002/anie.201511197,10.1039/c6cc06089g,10.1039/c6cc04531f,10.1039/c5cs00534e,10.1021/acs.joc.5b02557,10.1002/chem.201503596,10.1021/acs.chemrev.5b00386,10.1021/acs.orglett.5b02458,10.1002/adsc.201500304,10.1039/c4qo00321g,10.1021/jo502123k,10.1021/om500452c,10.1055/s-0034-1378208,10.1021/ja505823s,10.1021/ol501180q,10.1002/ejoc.201400126,10.1021/ja501649a,10.1002/aoc.3126,10.1021/jo500026g,10.1039/c3ob41989d,10.1016/j.molcata.2013.10.014,10.1016/j.tet.2013.09.039,10.1016/j.jorganchem.2013.06.001,10.1021/jo401032r,10.1002/chem.201300995,10.5059/yukigoseikyokaishi.71.588,10.1002/aoc.2964,10.1021/om3011855,10.1021/ja310848x,10.1021/ja308950d,10.1002/adsc.201200369,10.1021/jo300209d,10.1039/c2dt30886j,10.1021/ol202862t,10.1002/anie.201100683,10.1021/ol1018739,10.1039/c0cc03781h,10.1039/c004213g,10.1002/anie.200903146,10.1021/ja0713431,10.1021/jo0503557,10.1021/ja034908b,10.1016/S0040-4020(97)10233-2,10.1016/0022-328X(90)80270-ALong11/2/2021FALSE
308
325FALSEc4cc00716f10.1039/c4cc00716fhttps://sci-hub.wf/10.1039/c4cc00716fhttps://doi.org/10.1039/c4cc00716fNiC-H ActivationLongTRUE1209#N/A2014You, JS
Nickel-catalyzed chelation-assisted direct arylation of unactivated C(sp(3))-H bonds with aryl halides
CHEM COMMUN
In this work, we have disclosed the nickel-catalyzed unactivated beta-C(sp(3))-H bond arylation of aliphatic acid derivatives with aryl iodides/bromides via bidentate chelation-assistance of an 8-aminoquinoline moiety. These preliminary results indicate the intrinsic catalytic potential of nickel metal for unactivated C(sp(3))-H bond arylation.
Sichuan Univ2/19/2014Csp2_ar-Csp3E-NuXHIHArylAlkylNa2CO3Ionic-CO3_10.1002/ajoc.201700569,10.1021/acs.organomet.6b00529,10.1021/acs.orglett.6b02236,10.1021/acscatal.7b01044,10.1039/c5sc01589h,10.1039/c6qo00149a,10.1021/acs.joc.5b00669,10.1039/c5cc01436k,10.1039/c5sc03704b10.1021/acs.chemrev.1c00519,10.1039/d1cc05291h,10.1021/acs.organomet.1c00265,10.1016/j.tetlet.2021.152825,10.1021/acs.joc.0c00624,10.1055/s-0037-1610756,10.1080/00397911.2020.1761392,10.1002/anie.202003632,10.1002/cjoc.201900468,10.1002/slct.201904651,10.1021/acs.chemrev.9b00495,10.1002/tcr.201800093,10.1016/j.trechm.2019.06.002,10.1002/adsc.201900532,10.1002/ajoc.201900109,10.1039/c8sc05063e,10.1021/acs.orglett.9b00214,10.1039/c8qo01274a,10.1021/acsomega.9b00030,10.1021/acs.chemrev.8b00068,10.1021/acs.chemrev.8b00507,10.1021/acsomega.8b02430,10.1039/c8ob02237b,10.1021/jacs.8b07708,10.1039/c8ob01481g,10.1021/acs.organomet.8b00325,10.1039/c7sc04604a,10.1002/ajoc.201700569,10.1002/ejoc.201701215,10.1021/acscatal.7b02721,10.1002/chem.201704045,10.1039/c7sc01750b,10.1002/adsc.201700186,10.1039/c7cc04252c,10.1021/jacs.7b03548,10.1021/acs.joc.7b00582,10.1002/adsc.201700277,10.1002/chem.201605657,10.1039/c7cc02426f,10.1021/acscatal.7b01044,10.1002/cssc.201700321,10.1039/c7cc01097d,10.1002/adsc.201601121,10.1016/j.tetlet.2017.01.079,10.1002/ajoc.201600596,10.1021/acs.orglett.6b03856,10.1016/j.ejmech.2016.12.012,10.1021/acs.organomet.6b00529,10.1021/acs.joc.6b01831,10.1021/acscatal.6b02477,10.1002/ejoc.201601045,10.1016/j.tet.2016.08.010,10.1021/acs.orglett.6b02236,10.1007/s41061-016-0053-z,10.1021/acs.orglett.6b01041,10.1002/adsc.201600080,10.1021/jacs.6b02405,10.1021/acs.joc.5b02838,10.1002/adsc.201500727,10.1016/j.tetlet.2016.01.009,10.1021/acs.orglett.5b03593,10.1007/3418_2015_117,10.1039/c6qo00149a,10.1039/c5qo00421g,10.1039/c5sc03704b,10.1039/c6cc00822d,10.1002/ejoc.201501300,10.1039/c6ob00164e,10.1021/acs.orglett.5b03142,10.6023/A15040278,10.1002/adsc.201500701,10.1002/ejoc.201501186,10.1021/acs.joc.5b02138,10.1021/acs.orglett.5b02572,10.1016/j.tetlet.2015.09.038,10.1016/j.tet.2015.08.049,10.1021/jacs.5b07424,10.1016/j.jorganchem.2015.03.023,10.1002/chem.201502450,10.1021/acscatal.5b01075,10.1246/cl.150239,10.1016/j.tet.2015.03.085,10.1002/chem.201500639,10.1021/acs.joc.5b00669,10.1021/acs.orglett.5b01192,10.1021/acs.orglett.5b01128,10.1021/acs.joc.5b00580,10.1021/jacs.5b01671,10.1246/cl.150024,10.1021/acs.joc.5b00111,10.1021/acs.orglett.5b00471,10.1021/acs.joc.5b00025,10.1039/c5qo00104h,10.1039/c5sc01636c,10.1039/c5sc02143j,10.1039/c5sc01589h,10.1039/c5dt00032g,10.1039/c5ob00149h,10.1039/c5cc02254a,10.1039/c5cc01436k,10.3998/ark.5550190.p008.915,10.1039/c5cc01163a,10.1007/s10562-014-1449-4,10.1039/c4cc10446c,10.1002/ejoc.201403191,10.1039/c5qo00004a,10.1021/jo501697n,10.1021/jo501691f,10.1055/s-0034-1378555,10.1016/j.tetlet.2014.09.005,10.1055/s-0033-1338645,10.1039/c4cc03615h,10.6023/cjoc201405011,10.1002/chem.201403356,10.1002/chem.201403019,10.1039/c4cc07667b12/28/2021
309
237FALSEjo049940i10.1021/jo049940ihttps://sci-hub.wf/10.1021/jo049940ihttps://doi.org/10.1021/jo049940iNiC-O ActivationLongTRUE214341062004Percec, V
Nickel(0)-catalyzed cross-coupling of alkyl arenesulfonates with aryl Grignard reagents
JOURNAL OF ORGANIC CHEMISTRY
The nickel-catalyzed cross-coupling reactions of neopentyl arenesulfonates with arylmagnesium bromides, involving nucleophilic aromatic substitution of alkyloxysulfonyl groups by aryl nucleophiles, take place in high yields. Optimal efficiencies are obtained by adding 3 + 2 equiv of the Grignard reagent to a mixture of dppfNiCl(2) and the sulfonate in refluxing THF. Neopentyl arenesulfonates are useful sources of the electrophilic aryl groups in these transition metal-catalyzed cross-coupling reactions. Aryl sulfonates are inappropriate due to their ambident reactivity under the reaction conditions. This new cross-coupling reaction can be used for the creative elimination of alkyloxysulfonyl groups from aromatic compounds and for the preparation of unsymmetric terphenyls and oligophenyls.
Univ Penn5/14/2004Csp2_ar-Csp2_arE-NuOBOMsB(OH)2ArylArylK3PO4Ionic-PO4Weak0.36_xx10.1021/jo501291y,10.1021/ol101592r,10.1021/jo300547v,10.1016/j.tetlet.2006.01.145,10.1021/ol048490d,10.1021/jo7022558,10.1021/om300566m,10.1021/ol4011757,10.1055/s-2004-832818,10.1002/adsc.201000710,10.1039/c0cc03107k,10.1021/ja903091g,10.1002/ejoc.201200444,10.1002/adsc.201100151,10.1021/ol801972f,10.1021/acscatal.9b00744,10.1021/jacs.6b11412,10.1021/jacs.1c08502,10.1021/ol901217m,10.1021/jo3001194,10.1246/cl.2005.796,10.1021/jo2022982,10.1002/ejoc.201001519,10.1021/ja806244b,10.1002/chem.201000420,10.1021/jo202037x,10.1021/ol503061c,10.1021/ol9028308,10.1002/ejoc.200900067,10.1002/ejoc.201000147,10.1021/acscatal.5b01021,10.1021/ol401727y,10.1021/ol050393c,10.1039/c0cc02173c10.1021/jacs.1c08502,10.1002/ijch.202100057,10.1002/aoc.6378,10.1021/acs.joc.0c02663,10.17344/acsi.2021.6920,10.1002/chem.202004132,10.1021/acscatal.0c03334,10.1021/acs.orglett.0c01600,10.1016/j.chempr.2020.05.022,10.1021/acs.biomac.0c00507,10.1021/acs.biomac.9b01765,10.1002/ijch.202000004,10.1007/s10904-019-01288-9,10.1021/acs.biomac.9b01282,10.1515/pac-2019-0220,10.1134/S1070363219120405,10.1021/acs.oprd.9b00208,10.1021/acscatal.9b00744,10.1007/s00706-019-2364-6,10.1016/j.tet.2018.10.025,10.1021/acs.organomet.8b00244,10.1016/j.poly.2017.11.021,10.1002/adsc.201700838,10.1021/acs.organomet.7b00446,10.1021/acs.joc.6b03037,10.1038/s41570-017-0025,10.1021/jacs.6b11412,10.1002/ejic.201601351,10.1021/acscatal.6b02269,10.1016/j.tet.2016.10.018,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1002/adsc.201600024,10.1246/bcsj.20160100,10.1039/c5gc03012a,10.1021/acs.organomet.6b00059,10.1016/j.tetlet.2015.10.009,10.1021/jacs.5b01913,10.1002/anie.201505136,10.1002/ejoc.201500962,10.1002/ejoc.201500630,10.1021/acscatal.5b01021,10.1055/s-0034-1378867,10.1016/j.jorganchem.2015.04.019,10.1002/cctc.201403057,10.1002/aoc.3289,10.1016/j.catcom.2014.08.037,10.1039/c5ra12742d,10.1016/j.tetlet.2014.11.020,10.1021/ol503061c,10.1016/j.catcom.2014.08.010,10.1002/ejoc.201402881,10.1021/jo501835u,10.1002/ejoc.201402919,10.1016/j.tetlet.2014.07.118,10.1021/ol501600k,10.1007/s11426-014-5138-3,10.1021/jo501291y,10.1016/j.tet.2014.04.059,10.1002/ejoc.201402120,10.1002/chem.201304715,10.1021/cs4009946,10.1039/c4ra11520a,10.1002/asia.201300688,10.1016/j.inoche.2013.08.010,10.1080/00397911.2012.688160,10.1021/ol401727y,10.1021/ol4011757,10.1002/aoc.3000,10.1002/ajoc.201300031,10.1002/pola.26573,10.3390/molecules18021602,10.1039/c3ra44195d,10.1002/cctc.201200417,10.1039/c3cs35521g,10.1021/op300236f,10.1002/pola.26340,10.3390/molecules171012121,10.1021/om300566m,10.1021/jo301335x,10.6023/cjoc201206029,10.1021/om300399j,10.1021/jo300547v,10.1021/ol301681z,10.1002/ejoc.201200444,10.1021/om201101g,10.1021/jo300290v,10.1021/jo3001194,10.1021/om201271y,10.1021/jo2022982,10.1039/c2ob25225b,10.3987/COM-11-S(P)20,10.1039/c2cc15972d,10.1002/anie.201207428,10.1021/om200864z,10.1021/jo202037x,10.1002/adsc.201100151,10.1002/adsc.201100141,10.1002/adsc.201100101,10.1016/j.tetlet.2010.11.133,10.1016/j.jorganchem.2011.01.003,10.1021/ol200128y,10.1002/ejoc.201001519,10.1021/cr100259t,10.1021/cr1002276,10.1002/adsc.201000710,10.1021/jo101917x,10.1039/c0sc00498g,10.1002/anie.201007598,10.1039/c0cc02173c,10.1039/c1cs15114b,10.1002/chem.201002354,10.1002/chem.201002273,10.1021/ar100082d,10.1021/jo101718v,10.1021/ja108074t,10.3184/030823410X12887880118791,10.1021/ol101592r,10.1021/jo101023t,10.1021/jo100846t,10.1055/s-0030-1258116,10.1002/ejoc.201000147,10.1021/ja910808x,10.1021/ol9028308,10.1016/j.tetlet.2009.10.096,10.1039/c0cc03107k,10.1002/chem.201000420,10.1039/c0dt00021c,10.1021/om900771v,10.1021/ja907882n,10.1055/s-0029-1218283,10.1055/s-0029-1217032,10.1021/ol902155e,10.1002/adsc.200900480,10.1021/cr900157q,10.1021/om900460u,10.1021/ol9013359,10.1021/ol901217m,10.1021/cr900074m,10.1021/ja903091g,10.1055/s-0029-1216790,10.1002/ejoc.200900067,10.1021/om8010596,10.1016/j.jorganchem.2008.11.003,10.1021/ol802493z,10.1002/anie.200904033,10.1021/om800711g,10.1021/ol801972f,10.1021/ol802049t,10.1021/ja806244b,10.1021/ja8055358,10.1021/jo8014819,10.1002/adsc.200800414,10.1021/ja804672m,10.1016/j.tet.2008.01.050,10.1021/ol800832n,10.1021/ja711449e,10.1021/jo7022558,10.1002/anie.200802157,10.1002/anie.200803193,10.1039/b801888j,10.1021/om700796g,10.1021/jo7019064,10.1021/om700607m,10.1016/j.tetlet.2007.08.089,10.1055/s-2007-983845,10.1021/ja073714j,10.1021/jo0709448,10.1055/s-2007-965958,10.1016/j.tetlet.2007.01.175,10.1021/jo0623742,10.1002/chem.200600502,10.1002/chem.200601582,10.1002/ejoc.200600469,10.1016/j.ccr.2006.02.031,10.1016/j.tetlet.2006.07.085,10.1002/chem.200600178,10.1055/s-2006-942451,10.1002/adsc.200505409,10.1002/adsc.200606002,10.1002/ejoc.200600026,10.1016/j.tetlet.2006.01.145,10.1016/j.tetlet.2006.01.020,10.1021/jo052369i,10.1021/ic0518273,10.1021/om050781i,10.1021/jo0513764,10.1021/om050224w,10.1021/jo051394l,10.1021/ol051615+,10.1021/ol050393c,10.1246/cl.2005.796,10.1021/ol047854z,10.1002/anie.200461444,10.1039/b500952a,10.1055/s-2004-832818,10.1021/jo048572f,10.1021/ol048490dKelly11/30/2021
310
327FALSEanie.20130449210.1002/anie.201304492https://sci-hub.wf/10.1002/anie.201304492https://doi.org/10.1002/anie.201304492NiC-H ActivationGerryTRUE12217492013Yamaguchi, J
C-H Alkenylation of Azoles with Enols and Esters by Nickel Catalysis
ANGEW CHEM INT EDIT
Nagoya Univ9/16/2013Csp2_ar-Csp2E-NuOHOPivHHetVInylK3PO4Ionic-PO4Medium0.33_10.1021/acscatal.6b01120,10.1021/jacs.7b12865,10.1002/anie.201403823,10.1039/c4cc08426h,10.1002/anie.201510743,10.1021/acscatal.7b00941,10.1021/acscatal.8b04267,10.1039/c5sc02942b,10.1021/acscatal.6b00801,10.1021/acs.orglett.6b02656,10.1021/ja413131m,10.1021/acscatal.8b03436,10.1002/anie.201412051,10.1002/anie.202103327,10.1021/acscatal.9b00884,10.1002/chem.201702867,10.1021/acs.orglett.6b0226510.1039/d1sc06968c,10.1016/j.chempr.2021.08.001,10.1002/adsc.202100992,10.1021/acscatal.1c01850,10.1002/chem.202100475,10.1002/tcr.202100113,10.1002/anie.202103327,10.1055/a-1484-6216,10.1021/acs.orglett.1c00940,10.1002/anie.202100949,10.1039/d0sc06868c,10.1039/d0cc08389e,10.6023/cjoc202008044,10.1021/acs.chemrev.0c00153,10.1055/a-1349-3543,10.1021/acs.orglett.0c03342,10.3390/molecules25214970,10.1021/acscatal.0c03334,10.1055/s-0040-1705943,10.1002/asia.202000763,10.1021/acs.chemrev.9b00682,10.1021/acs.orglett.0c01469,10.1039/d0ob00789g,10.1021/acs.orglett.0c01127,10.1016/j.chempr.2020.04.005,10.1002/anie.201913930,10.1002/adsc.201901078,10.1021/jacs.9b08586,10.1002/anie.201911372,10.1021/acs.orglett.9b03170,10.1021/acs.organomet.9b00060,10.1007/s10593-019-02475-9,10.1021/acscatal.9b00884,10.1039/c9cy00009g,10.1039/c8cc09165j,10.3390/catal9010076,10.1021/acscatal.8b04267,10.1021/acscatal.8b03436,10.1021/acscatal.8b03770,10.1016/j.bmc.2018.04.007,10.1002/asia.201800478,10.1039/c8ob01034j,10.1246/cl.180226,10.3762/bjoc.14.60,10.1021/acs.orglett.8b00530,10.1021/jacs.7b12865,10.1002/chem.201705842,10.1021/acs.orglett.7b03713,10.1021/acs.orglett.8b00080,10.1039/c7dt04560c,10.1021/acs.orglett.7b03669,10.1016/S1872-2067(17)62985-1,10.1002/adsc.201701105,10.1055/s-0036-1591495,10.1055/s-0036-1589120,10.1021/acs.joc.7b01686,10.1039/c7cs00182g,10.1039/c7ob01838j,10.1002/chem.201702867,10.1021/acs.orglett.7b01905,10.1021/acs.orglett.7b01938,10.1021/acscatal.7b00941,10.1021/acs.orglett.7b01194,10.1038/ncomms14993,10.1016/j.tet.2017.02.021,10.1246/bcsj.20160365,10.1016/j.catcom.2017.02.001,10.1021/jacs.7b00049,10.1021/acscatal.7b00245,10.1246/cl.161001,10.1021/acs.orglett.6b02656,10.1021/acscatal.6b02477,10.1021/acs.orglett.6b02619,10.1016/j.tet.2016.07.082,10.1021/acs.orglett.6b02265,10.1002/chem.201603092,10.1007/s41061-016-0053-z,10.1002/anie.201603068,10.1021/acscatal.6b00801,10.1021/acscatal.6b01120,10.1021/acs.joc.6b00715,10.1246/cl.160133,10.1002/adsc.201500822,10.1002/anie.201510743,10.1039/c6np00067c,10.1039/c6ra07130a,10.1515/hc-2015-0137,10.1002/ejoc.201500630,10.1002/anie.201503204,10.1016/j.tet.2015.03.066,10.1038/ncomms8508,10.1002/anie.201412319,10.1002/anie.201412051,10.1021/acs.orglett.5b00517,10.1021/jo502761x,10.1021/ja5116452,10.1039/c5sc02942b,10.1039/c5cc02254a,10.3998/ark.5550190.p008.915,10.1039/c4ra13761b,10.1007/s10562-014-1449-4,10.1039/c4cc08426h,10.1039/c4cc10084k,10.1039/c4dt02313g,10.1002/chem.201405119,10.1021/jo501361k,10.1021/ol5019135,10.1002/anie.201403823,10.1021/ja412563e,10.1021/ja413131m,10.1021/ja4118413,10.1021/ja410883p,10.1039/c4ra09092f,10.1039/c3cc48750d,10.1039/c4cs00206g,10.1021/ja409803x11/22/2021
311
163FALSEjo070912k10.1021/jo070912khttps://sci-hub.wf/10.1021/jo070912khttps://doi.org/10.1021/jo070912kNiC-O ActivationLongTRUE836582007
Skrydstrup, T
NiCl2(dppe)-catalyzed cross-coupling of aryl mesylates, arenesulfonates, and halides with arylboronic acids
JOURNAL OF ORGANIC CHEMISTRY
An investigation of the NiCl2(dppe)-, NiCl2(dppb)-, NiCl2(dppf)-, NiCl2(PCy3)(2)-, and NiCl2(PPh3)(2)-catalyzed cross-coupling of the previously unreported aryl mesylates, and of aryl arenesulfonates, chlorides, bromides, and iodides containing electron-withdrawing and electron-donating substituents with aryl boronic acids, in the absence of a reducing agent, is reported. NiCl2(dppe) was the only catalyst that exhibited high and solvent-independent activity in the two solvents investigated, toluene and dioxane. NiCl2(dppe) with an excess of dppe, NiCl2(dppe)/dppe, was reactive in the cross-coupling of electron-poor aryl mesylates, tosylates, chlorides, bromides, and iodides. This catalyst was also efficient in the cross-coupling of aryl bromides and iodides containing electron-donating substituents. Most surprisingly, the replacement of the excess dppe from NiCl2(dppe)/dppe with excess PPh3 generated NiCl2(dppe)/PPh3, which was found to be reactive for the cross-coupling of both electron-rich and electron-poor aryl mesylates and chlorides. Therefore, the solvent-independent reactivity of NiCl2(dppe) provides an inexpensive and general nickel catalyst for the cross-coupling of aryl mesylates, tosylates, chlorides, bromides, and iodides with aryl boronic acids.
Aarhus Univ8/17/2007Csp2-Csp2_arE-NuOB
OPO(OPh)2
B(OH)2VinylArylK3PO4Ionic-PO4Strong0.04_10.1021/jacs.8b02134,10.1021/acscatal.7b04030,10.1021/jacs.6b11412,10.1002/chem.201000420,10.1021/ol4011757,10.1021/jo200003410.1016/j.tet.2021.132513,10.1002/chem.202004132,10.1039/d0cy01159b,10.1021/acs.joc.0c01254,10.1021/acs.orglett.0c01123,10.1021/acs.joc.9b02880,10.1002/cjoc.201800554,10.1002/cctc.201900132,10.1039/c8ob01533c,10.1134/S1070428018070047,10.1021/jacs.8b02134,10.1021/acscatal.7b04030,10.1016/j.jorganchem.2017.07.006,10.1002/aoc.3705,10.6023/cjoc201611018,10.1021/jacs.6b11412,10.1002/slct.201601789,10.1002/anie.201604406,10.1016/j.tet.2016.04.018,10.1055/s-0035-1560397,10.1007/s00706-015-1613-6,10.1039/c6ra14678c,10.1002/anie.201506437,10.1055/s-0035-1560175,10.1016/j.tetlet.2015.10.022,10.1016/j.tetlet.2015.10.009,10.1002/anie.201502379,10.1002/ajoc.201500044,10.1016/j.tetasy.2014.12.010,10.1039/c5ra12742d,10.1039/c5ra01363a,10.3390/ecsoc-19-a031,10.1002/ejoc.201402202,10.1166/jnn.2014.9013,10.1039/c4ra07455f,10.1055/s-0033-1339334,10.1021/ol4011757,10.1002/hlca.201200454,10.1039/c3cs35521g,10.1016/j.tet.2012.06.037,10.1016/j.tetasy.2012.06.024,10.1021/ol3010112,10.1055/s-0031-1290504,10.1021/ja301243t,10.1055/s-0031-1289717,10.1055/s-0031-1290751,10.1021/om200787s,10.1002/asia.201100147,10.1002/adsc.201100101,10.1021/jo2000034,10.1016/j.tetlet.2011.01.113,10.1021/cr100259t,10.1021/cr100327p,10.1039/c1cs15100b,10.1002/chem.201002273,10.1055/s-0030-1259104,10.1002/ejoc.201000928,10.1002/ijch.201000031,10.1021/ol9028034,10.1002/anie.201002745,10.1002/anie.201001799,10.1002/chem.201000420,10.1055/s-0029-1217067,10.1021/ol901975u,10.1016/j.tet.2009.06.101,10.1021/ja904152r,10.1021/jo900098a,10.1021/jo900291f,10.1021/jo802460z,10.1021/jo801824e,10.1021/jo801985a,10.3987/COM-08-S(N)40,10.1055/s-2008-1067193,10.1021/jo800444y,10.1021/jo7027097,10.1021/jo7026189,10.1002/anie.200705558,10.1002/chem.200800608,10.1039/b705664h Long 12/15/2021
312
206FALSEjo102446410.1021/jo1024464https://sci-hub.wf/10.1021/jo1024464https://doi.org/10.1021/jo1024464NiC-O ActivationShihongTRUE11521822011Kappe, CO
Investigations on the Suzuki-Miyaura and Negishi couplings with alkenyl phosphates: Application to the synthesis of 1,1-disubstituted alkenes
JOURNAL OF ORGANIC CHEMISTRY
The development of versatile Suzuki-Miyaura and Negishi cross-couplings with nonactivated alkenyl phosphates and aromatic boronic acids or organozinc reagents was achieved in acceptable to good yields. A series of 1,1-disubstituted alkenes were synthesized using a combination of either Ni(COD)(2)/Cy3P/ K3PO4 or Pd(2)dba(3)/DPPF in THF. When working with alkenyl electrophiles in metal-catalyzed cross-couplings, this method lends itself as a less costly and more stable alternative to the corresponding triflate or nonaflate derivatives. In addition, initial studies are presented regarding an efficient 1,2-migration under Negishi coupling conditions.
Karl Franzens Univ Graz
3/4/2011Csp2_ar-Csp2_arE-NuOB
OCONEt2
B(OH)2ArylArylK3PO4Ionic-PO4Medium0.31TM10.1002/anie.201101461,10.1021/ol203322v,10.1021/jo2022982,10.1021/jacs.0c06995,10.1021/jo202037x,10.1021/ja200398c,10.1021/om500452c,10.1021/jo300547v,10.1002/adsc.201100151,10.1002/ejoc.201200444,10.1021/acs.orglett.6b01398,10.1021/ol301847m,10.1021/jo501291y,10.1021/acscatal.5b01021,10.1021/acs.joc.6b01627,10.1021/jo4005537,10.1021/ja2084509,10.1021/acscatal.9b00744,10.1039/c4qo00321g,10.1021/jo3001194,10.1021/ol401727y10.1002/ajoc.202200023,10.1039/d1nj03380h,10.1016/j.poly.2021.115387,10.1055/a-1548-8362,10.1055/a-1503-6330,10.1055/a-1349-3543,10.1080/14756366.2021.1900165,10.1002/chem.202004132,10.1002/aoc.6012,10.1021/acs.chemrev.0c00088,10.1021/jacs.0c06995,10.1016/j.mcat.2020.111048,10.1039/d0nj01610a,10.1002/aoc.5662,10.1016/j.mcat.2020.110841,10.1021/acsomega.9b04450,10.1002/chem.201904845,10.3390/catal10010136,10.1021/acscatal.9b02316,10.1002/app.48200,10.1039/c9ob00313d,10.1021/acscatal.9b00744,10.1007/3418_2018_19,10.1002/tcr.201800045,10.1016/j.tet.2018.10.025,10.1021/acs.jpcc.8b07538,10.3390/molecules23102435,10.1016/j.tet.2018.02.053,10.1038/s41598-018-21366-1,10.1039/c7qi00694b,10.1016/j.matpr.2017.11.256,10.1055/s-0036-1588508,10.3390/catal7040098,10.1021/acscatal.6b02912,10.1039/c6nj03789e,10.1002/adsc.201601105,10.2174/1570179413666160624092044,10.1016/j.jorganchem.2016.09.026,10.1021/acs.joc.6b01627,10.1021/acs.orglett.6b02550,10.1055/s-0035-1562484,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1021/acs.orglett.6b01398,10.1021/acs.orglett.5b03712,10.1016/j.saa.2015.10.015,10.1016/bs.adomc.2016.07.001,10.6023/cjoc201507008,10.1039/c5ra25752b,10.1002/ejoc.201500987,10.1021/acscatal.5b01021,10.1016/j.tet.2015.02.088,10.3390/molecules20057528,10.1016/j.jorganchem.2015.01.009,10.3390/catal5010018,10.1021/ol503560e,10.1021/jo5024393,10.1071/CH15459,10.1039/c4qo00321g,10.1039/c4cy01736f,10.1039/c5ra12512j,10.1016/j.saa.2014.04.185,10.1021/om500452c,10.1007/s11426-014-5138-3,10.1021/jo501291y,10.1002/ejoc.201402120,10.1021/cr400230c,10.1021/cs4009946,10.3184/174751914X13857348538466,10.6023/cjoc201307035,10.1039/c3ob41382a,10.1002/chem.201303638,10.1002/ejoc.201300592,10.1002/asia.201300688,10.1002/aoc.3020,10.1021/ol401727y,10.1021/ar300318c,10.1021/jo4005537,10.1021/ol401021x,10.3998/ark.5550190.0014.219,10.1039/c3cs35521g,10.1002/ejoc.201200914,10.1021/op300236f,10.1016/j.tetlet.2012.09.127,10.1002/adsc.201200334,10.1002/adsc.201200364,10.1021/ol301847m,10.1021/jo300547v,10.1021/ol301681z,10.1002/ejoc.201200444,10.1002/ejoc.201200368,10.1021/ol301275u,10.1021/jo300437t,10.1021/jo3001194,10.1021/om201271y,10.1021/ol203322v,10.1021/jo2022982,10.1021/ja2084509,10.1039/c2gc16111g,10.1002/anie.201202136,10.1021/jo202037x,10.1021/om2003706,10.1002/adsc.201100151,10.1021/op200090k,10.1021/ja200398c,10.1002/anie.2011014611/6/2022
313
330FALSEol900778m10.1021/ol900778mhttps://sci-hub.wf/10.1021/ol900778mhttps://doi.org/10.1021/ol900778mNiC-H ActivationGerryTRUE12411#N/A2009
Yamakawa, T
CP2Ni-KOt-Bu-BEt3 (or PPh3) Catalyst System for Direct C-H Arylation of Benzene, Naphthalene, and PyridineORG LETT
Ni-catalyzed direct C-H arylation of benzene and naphthalene using aryl halides was investigated. For the first time, the arylation was successfully catalyzed by Cp2Ni (5 mol %) in the presence of KOt-Bu and BEt3. This Ni catalyst system was also applied to direct C-H arylation of pyridine, an electron-deficient heteroarene; PPh3 was used instead of BEt3 in this case.
Sagami Chem Res Ctr
6/18/2009Csp2_ar-Csp2_arE-NuXHXHArylHetKOtBuIonic-OtBu_xx10.1021/ol901684h,10.1021/ja9053509,10.1021/ja306062c,10.1002/asia.201100971,10.1002/anie.200906996,10.1002/chem.201101091,10.1016/j.tet.2013.04.096,10.1002/cctc.201000223,10.1039/c1cc16582h,10.1021/ja210249h,10.1002/chem.20100163110.1039/d0tc05527a,10.1021/acs.joc.0c02069,10.1002/ajoc.202000443,10.1021/acs.chemrev.9b00682,10.1016/j.chempr.2020.04.005,10.1039/d0ra01845g,10.1002/cplu.202000005,10.1002/ajoc.201900554,10.1039/c9ra07044c,10.1021/acs.joc.9b02094,10.1002/ejoc.201900067,10.1021/acs.chemrev.8b00507,10.3390/catal9010076,10.1021/acs.accounts.8b00408,10.1039/c7dt04560c,10.1021/acs.joc.7b02004,10.1016/j.jorganchem.2017.05.035,10.1021/acs.chemrev.7b00021,10.1002/chem.201605657,10.1002/cssc.201700321,10.1021/acscatal.7b00397,10.3762/bjoc.12.272,10.1021/acs.joc.6b01329,10.1002/cjoc.201600442,10.1016/j.tetlet.2016.08.034,10.1021/acs.joc.6b01103,10.1007/s41061-016-0053-z,10.1016/j.tet.2015.04.044,10.1021/acs.orglett.5b03712,10.1021/acs.joc.5b01391,10.1055/s-0034-1380923,10.1002/ejoc.201500630,10.1016/j.tet.2015.05.082,10.1002/aoc.3300,10.1016/j.tet.2015.03.049,10.1016/j.tetlet.2015.01.131,10.1039/c5qo00236b,10.1039/c5dt00032g,10.1039/c4sc03051f,10.1002/cjoc.201400528,10.1016/j.tetlet.2014.09.043,10.1002/ejoc.201402881,10.1055/s-0034-1378552,10.1021/ol502370r,10.1002/cctc.201402020,10.1002/chem.201304459,10.1002/adsc.201300865,10.1246/bcsj.20130166,10.1002/asia.201301371,10.1021/ol403311b,10.1002/adsc.201300922,10.1039/c4ra07688e,10.1039/c4cc02546f,10.1039/c4dt00155a,10.1021/ja409803x,10.1002/jhet.2005,10.1021/ja408112j,10.1021/ol4022904,10.1002/ajoc.201300129,10.1016/j.tet.2013.04.096,10.1021/jo400152f,10.1039/c2ob27325j,10.1002/anie.201208666,10.1002/ejoc.201200914,10.6023/cjoc1201291,10.1021/ja306062c,10.1002/adsc.201200195,10.1016/j.tetlet.2012.05.073,10.1016/j.tet.2012.05.040,10.1002/asia.201100971,10.1021/om300147y,10.1002/chem.201103748,10.2174/157019312799079884,10.1002/cctc.201100320,10.1021/ja210249h,10.1016/j.tet.2011.10.049,10.1039/c2cc16790e,10.1002/anie.201106825,10.1002/anie.201203269,10.1039/c1cc16582h,10.1039/c2cc35468c,10.1021/om200819c,10.1021/ja209510q,10.1021/ja208129t,10.1021/jo201501f,10.1021/jo2013324,10.1055/s-0030-1260169,10.1021/ja206850s,10.1016/j.tetlet.2011.07.046,10.1021/ja206572w,10.1002/tcr.201100023,10.1002/chem.201101091,10.1246/cl.2011.555,10.1021/ja2021075,10.1016/j.molcata.2011.03.007,10.1002/adsc.201000723,10.1016/j.tetlet.2010.12.092,10.1021/cs1001543,10.1002/chem.201002290,10.1002/chem.201002309,10.1002/anie.201103720,10.1021/ja103050x,10.1002/cctc.201000223,10.5059/yukigoseikyokaishi.68.1132,10.1021/ja107541w,10.1021/ja105368p,10.1021/jo9025622,10.1021/ol902537d,10.1002/anie.200906870,10.1002/anie.200906996,10.1002/anie.201004097,10.1002/chem.201001631,10.1039/c0dt00486c,10.1039/c0dt00104j,10.1039/c0ob00176g,10.1016/j.tet.2009.10.015,10.1055/s-0029-1217131,10.1021/ol901684h,10.1021/ja905350912/29/2021
314
331FALSEjacs.7b0344810.1021/jacs.7b03448https://sci-hub.wf/10.1021/jacs.7b03448https://doi.org/10.1021/jacs.7b03448NiC-N ActivationLongTRUE1847#N/A2017Doylet, AG
Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines
J AM CHEM SOC
A Ni-catalyzed reductive cross-coupling of styrenyl aziridines with aryl iodides is reported. This reaction proceeds by a stereoconvergent mechanism and is thus amenable to asymmetric catalysis using a chiral BiOxazoline ligand for Ni. The process allows facile access to highly enantioenriched 2-arylphenethylamines from racemic aziridines. Multivariate analysis revealed that ligand polarizability, among other features, influences the observed enantioselectivity, shedding light on the success of this emerging ligand class for enantioselective Ni catalysis.
Princeton Univ4/26/2017TRUETRUEFALSECsp3-Csp2_arE-ENX
N(Ring-Opening)
IAlkylArylNo baseNo Base_xx10.1038/s41467-019-11392-6,10.1021/acs.orglett.8b03367,10.1126/sciadv.aaw9516,10.1021/jacs.8b13524,10.1021/jacs.9b03863,10.1021/jacs.0c13093,10.1039/c9cc08079a10.1039/d2re00030j,10.1021/acs.orglett.2c00217,10.1002/cjoc.202100819,10.1055/s-0041-1737762,10.1021/jacs.1c10932,10.1021/acscatal.1c04235,10.1002/ejic.202100707,10.1039/d1qo01406d,10.1021/acscatal.1c04128,10.1038/s41467-021-26794-8,10.6023/A21070345,10.1039/d1sc05451a,10.1021/acscatal.1c04143,10.1021/jacs.1c08105,10.1021/jacs.1c08695,10.1002/wcms.1573,10.1021/acs.orglett.1c02514,10.1002/tcr.202100210,10.1021/jacs.1c07139,10.1021/jacs.1c05670,10.1038/s41557-021-00746-7,10.1021/jacs.1c03763,10.1021/acs.orglett.1c01821,10.1039/c9cs00571d,10.1021/jacs.1c03827,10.1021/acs.chemrev.0c00844,10.1002/anie.202102769,10.1021/jacs.1c03527,10.1039/d1sc00943e,10.1021/acs.orglett.1c01077,10.1002/adsc.202100195,10.1021/acs.organomet.0c00775,10.1002/anie.202101076,10.1021/jacs.1c01916,10.1038/s41570-021-00260-x,10.1021/jacs.0c13093,10.1002/adsc.202001423,10.1038/s41467-020-20888-5,10.1021/jacs.0c12843,10.1021/acs.orglett.0c03865,10.2174/1570179418666210224124931,10.1002/anie.202013679,10.1021/jacs.0c08823,10.1021/acs.oprd.0c00367,10.1021/acs.inorgchem.0c01917,10.1021/acscatal.0c03237,10.1021/acscatal.0c03341,10.1002/ejic.202000782,10.1021/acscatal.0c01842,10.1021/acs.joc.0c01274,10.1016/j.eurpolymj.2020.109900,10.1039/d0sc02065f,10.1021/acs.joc.0c00899,10.1055/s-0039-1690857,10.1021/jacs.0c03708,10.1039/d0ob00535e,10.1021/acscatal.0c01199,10.1021/jacs.0c01724,10.1002/slct.201903359,10.1021/acs.joc.0c00010,10.1039/c9cc10089j,10.1039/d0qo00072h,10.1002/cctc.201902069,10.1021/acs.joc.9b02603,10.1021/acs.chemrev.9b00425,10.1002/anie.201914175,10.1039/c9cc08079a,10.1021/acscatal.9b04823,10.1002/chem.201905048,10.1039/c9qo01033e,10.1016/j.trechm.2019.08.004,10.1039/c9cy01670h,10.1002/asia.201901067,10.1002/anie.201910168,10.1039/c9sc02507c,10.1021/acs.joc.9b01556,10.1038/s41467-019-11392-6,10.1002/adsc.201900028,10.1021/acs.orglett.9b02058,10.1021/acscatal.9b01347,10.1021/jacs.9b05934,10.1021/acs.orglett.9b01987,10.1002/chem.201902009,10.1021/acs.orglett.9b01496,10.1126/sciadv.aaw9516,10.1021/jacs.9b03863,10.1021/acscatal.9b01191,10.1021/acs.orglett.9b00692,10.1021/jacs.9b00931,10.1002/chem.201805987,10.1039/c8ob03029d,10.1002/anie.201900228,10.1055/s-0037-1611669,10.1021/jacs.8b13524,10.1039/c8sc04335c,10.1021/acs.organomet.8b00720,10.1021/acs.orglett.8b03367,10.1021/jacs.8b10217,10.1039/c8qo01044g,10.1021/acscatal.8b03930,10.1039/c8cc07093h,10.1038/s41467-018-07198-7,10.1038/s41570-018-0040-8,10.1021/acscatal.8b02784,10.1039/c8sc02223b,10.1002/anie.201806780,10.1021/jacs.8b05340,10.1002/anie.201803228,10.1021/jacs.8b05650,10.1021/acs.orglett.8b01394,10.1039/c7sc05320g,10.1002/anie.201712395,10.1246/cl.171130,10.1002/cjoc.201700745,10.1021/jacs.7b12212,10.1039/c7cc08928g,10.1021/acs.accounts.7b00432,10.1039/c7sc03404k,10.1021/acs.orglett.7b03747,10.1055/s-0036-1589102,10.1039/c7ob02167d,10.1021/jacs.7b06469,10.1021/jacs.7b06723,10.1038/s41570-017-0065,10.1021/acs.orglett.7b02076,10.1021/acs.orglett.7b01333,10.1021/jacs.7b04203,10.1021/jacs.7b0170511/11/2021APR 262017FALSEFALSEFALSEFALSE139165688
315
178FALSEjo200003410.1021/jo2000034https://sci-hub.wf/10.1021/jo2000034https://doi.org/10.1021/jo2000034NiC-O ActivationLongTRUE9214462011Zhao, YF
Rapid Nickel-Catalyzed Suzuki-Miyaura Cross-Couplings of Aryl Carbamates and Sulfamates Utilizing Microwave Heating
JOURNAL OF ORGANIC CHEMISTRY
High-speed and scalable nickel-catalyzed cross-coupling of arylboronic acids with aryl carbamates and sulfamates is achieved by using sealed-vessel microwave processing.
Xiamen Univ4/1/2011yCsp2_ar-Csp2_arE-NuOB
OP(O)(OEt)2
B(OH)2ArylArylK3PO4Ionic-PO4Strong0.04TMxxx10.1002/adsc.201400460,10.1021/jacs.6b11412,10.1021/om500452c,10.1021/jo300547v,10.1021/jo3001194,10.1002/ejoc.201200444,10.1039/c7cc06717h,10.1021/ja210249h,10.1039/c4qo00321g,10.1021/ol201437g,10.1021/acs.joc.6b01627,10.1021/jacs.7b04973,10.1021/jo4005537,10.1021/jo202298210.1021/acs.inorgchem.1c03042,10.1021/acsanm.1c03169,10.1016/j.tetlet.2021.153572,10.1021/acs.inorgchem.1c03042,10.1080/10426507.2021.2012178,10.1039/d1ra04947j,10.1002/chem.202005426,10.1055/a-1349-3543,10.1002/chem.202004132,10.1002/aoc.5662,10.1002/cjoc.201900506,10.1021/acsomega.9b04450,10.1002/ejoc.201901362,10.1021/acs.joc.9b00669,10.1039/c9ob00313d,10.1055/s-0037-1611720,10.1016/j.tet.2018.10.025,10.1039/c8ob01034j,10.3390/molecules23071715,10.1016/j.jorganchem.2018.01.019,10.1016/j.tet.2018.02.053,10.1002/aoc.4273,10.1002/anie.201711599,10.1039/c7cc06717h,10.1055/s-0036-1588508,10.1021/jacs.7b04973,10.1021/acsomega.7b01165,10.1038/s41570-017-0025,10.1021/jacs.6b11412,10.1021/acscatal.6b02964,10.1002/slct.201601789,10.1021/acs.joc.6b01627,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1021/acs.orglett.5b03712,10.1007/s00706-015-1613-6,10.1039/c6dt02995g,10.1055/s-0035-1560175,10.1016/j.tetlet.2015.10.009,10.1021/acs.joc.5b01559,10.1002/ejoc.201500630,10.1021/acs.joc.5b00771,10.1002/ajoc.201500044,10.3390/molecules20057528,10.1021/acs.jpca.5b00569,10.1016/j.jorganchem.2015.01.009,10.1021/ol503560e,10.1071/CH15459,10.1039/c4qo00321g,10.1039/c5ra03334a,10.1055/s-0034-1379366,10.1021/om500452c,10.1002/adsc.201400460,10.1007/s11426-014-5138-3,10.1021/ol500838h,10.1002/ejoc.201402120,10.3762/bjoc.10.117,10.1021/ja4118413,10.1021/cs4009946,10.1021/jo402392t,10.1021/jo402307x,10.3184/174751914X13857348538466,10.6023/cjoc201307035,10.1039/c3ra45212c,10.1016/j.tetlet.2013.10.031,10.1039/c3ob41382a,10.1021/ja409803x,10.1002/ejoc.201300592,10.1002/asia.201300688,10.1002/aoc.3020,10.1021/ol401341s,10.1021/jo4005537,10.1002/adsc.201200929,10.1039/c3sc00052d,10.1039/c3cs35521g,10.1021/op300236f,10.1016/j.tetlet.2012.09.127,10.1002/ejic.201200988,10.1002/adsc.201200364,10.1021/jo301270t,10.1021/jo300547v,10.1002/ejoc.201200444,10.1002/ejoc.201200368,10.1021/jo300290v,10.1021/jo3001194,10.1021/jo2022982,10.1021/ja210249h,10.1021/ol201437gKelly12/2/2021
316
333FALSEja501093m10.1021/ja501093mhttps://sci-hub.wf/10.1021/ja501093mhttps://doi.org/10.1021/ja501093mNiC-N ActivationShihongTRUE2461792014Yoshida, J
Direct C-N Coupling of Imidazoles with Aromatic and Benzylic Compounds via Electrooxidative C-H Functionalization
J AM CHEM SOC
A method for the C-N coupling of imidazoles based on electrooxidative C-H functionalization of aromatic and benzylic compounds has been developed. The key to the success is the formation of protected imidazolium ions as initial products, avoiding overoxidation. Deprotection under nonoxidative conditions affords N-substituted imidazoles. Various functional groups are compatible with the present transformation. To demonstrate the power of the method, a P450 17 inhibiter and an antifungal agent having N-substituted imidazole structures were synthesized.
Kyoto Univ3/26/2014Csp2_ar-Csp2_arE-NuOMgOMeMgXArylArylNo baseNo BaseStrong-0.28_10.1016/j.trechm.2021.12.008,10.1021/acsomega.1c06029,10.1039/d1gc02821a,10.1021/acs.joc.1c01409,10.1021/acs.joc.1c00944,10.1002/adsc.202100264,10.1002/ejoc.202100269,10.1002/adsc.202100236,10.1007/s11426-020-9938-9,10.1002/ejoc.202100113,10.1039/d1re00058f,10.1002/adsc.202001581,10.1002/aoc.6156,10.1002/cjoc.202000407,10.1039/d0sc01848a,10.1002/chem.202003852,10.1021/acs.orglett.0c03283,10.1002/ejoc.202001066,10.1021/jacs.0c08437,10.1080/00397911.2020.1781185,10.1039/d0ra03096a,10.1039/d0ob00441c,10.1002/chem.201904750,10.1016/j.electacta.2020.135786,10.1002/chem.201905774,10.1016/bs.aihch.2019.11.002,10.1039/c9cc08622f,10.1021/acs.orglett.9b03696,10.1002/anie.201910395,10.1038/s41467-019-13024-5,10.1021/jacs.9b07323,10.1039/c9gc01391a,10.1002/celc.201900117,10.1021/acs.orglett.9b01910,10.1002/celc.201900435,10.1002/anie.201901762,10.1055/s-0037-1611568,10.1021/acs.orglett.9b00947,10.1038/s41557-019-0254-5,10.1039/c9cc00975b,10.1039/c8gc03622e,10.1038/s41929-019-0231-9,10.1021/acs.joc.8b03014,10.1021/acs.joc.8b02191,10.1038/s41467-019-08414-8,10.1021/acs.orglett.8b03191,10.1002/chem.201804157,10.1002/chem.201802706,10.6023/cjoc201804001,10.1038/nrd.2018.116,10.1039/c7cs00619e,10.1002/chem.201802247,10.1021/acscatal.8b01682,10.1021/acscatal.8b01697,10.3987/COM-18-13942,10.1021/acs.chemrev.8b00233,10.1039/c8gc01411f,10.1002/anie.201711060,10.1002/anie.201801106,10.1002/chem.201801108,10.1021/acs.chemrev.7b00475,10.1002/anie.201800240,10.1002/anie.201707584,10.1002/adsc.201701401,10.1002/cjoc.201700740,10.1021/acscatal.7b04137,10.1016/j.chempr.2017.10.001,10.5796/electrochemistry.18-6-E2671,10.1039/c7gc03141f,10.1021/acscatal.7b03551,10.1021/acs.orglett.7b03152,10.1021/acs.chemrev.7b00397,10.1002/anie.201707906,10.1126/sciadv.aao3920,10.1002/celc.201700476,10.1039/c7cc04955b,10.1021/acs.chemrev.6b00620,10.1016/j.tet.2017.03.038,10.1021/acs.orglett.7b00746,10.1016/j.chempr.2017.02.006,10.1021/jacs.6b12708,10.1021/jacs.7b01016,10.1002/chem.201604484,10.1080/02603594.2016.1183487,10.1002/chem.201603783,10.1021/acs.joc.6b01595,10.1021/jacs.6b08856,10.1021/acs.chemrev.6b00057,10.1002/anie.201602616,10.1021/jacs.6b05273,10.1021/acs.joc.6b00615,10.1021/acscentsci.6b00091,10.1002/ejoc.201600048,10.1021/acs.orglett.5b03581,10.1021/acscatal.5b02417,10.1002/anie.201508035,10.1039/c6gc01970f,10.1039/c5cs00628g,10.1039/c5gc02626a,10.1039/c6gc00666c,10.1021/acs.joc.5b02222,10.6023/cjoc201504028,10.1002/anie.201412302,10.1126/science.aac9895,10.1016/j.tet.2015.05.096,10.1021/jacs.5b06526,10.1246/bcsj.20150100,10.3762/bjoc.11.105,10.1021/acs.accounts.5b00057,10.1002/anie.201502638,10.1002/ejoc.201500010,10.1002/anie.201412391,10.1021/ar500434f,10.1002/chem.201406398,10.1021/jo5022184,10.1016/j.jelechem.2014.09.018,10.1246/cl.140915,10.1039/c5gc01142f,10.3998/ark.5550190.0016.107,10.1021/cs5009909,10.1002/anie.201407948,10.1021/jo501736w1/6/2022
317
157FALSEjo202037x10.1021/jo202037xhttps://sci-hub.wf/10.1021/jo202037xhttps://doi.org/10.1021/jo202037xNiC-O ActivationLongTRUE81111062011Percec, V
Nickel-Catalyzed Cross-Coupling of Aryl Phosphates with Arylboronic Acids
JOURNAL OF ORGANIC CHEMISTRY
The Suzuki-Miyaura cross-coupling of aryl phosphates using Ni(PCy(3))(2)Cl(2) as an inexpensive, bench-stable catalyst is described. Broad substrate scope and high efficiency are demonstrated by the syntheses of more than 40 biaryls and by constructing complex organic molecules. The poor reactivity of aryl phosphates relative to aryl halides is successfully employed to construct polyarenes by selective cross-coupling using Pd and Ni catalysts.
Univ Penn12/16/2011Csp2_ar-Csp2_arE-NuOBOMsB(nep)ArylArylK3PO4Ionic-PO4Weak0.36TM10.1021/jo501291y,10.1021/jo300547v,10.1021/jacs.1c08502,10.1021/ol301847m,10.1021/jo3001194,10.1021/jo2022982,10.1021/acscatal.9b00744,10.1021/ol503061c,10.1021/acscatal.5b01021,10.1021/jacs.6b11412,10.1002/ejoc.20120044410.1021/jacs.1c08502,10.1016/j.jorganchem.2021.122068,10.1002/ijch.202100057,10.1021/acscatal.0c03334,10.1021/acs.joc.0c00929,10.1016/j.polymer.2020.122611,10.1016/j.mcat.2020.110915,10.1021/acs.biomac.0c00507,10.1021/acs.biomac.9b01765,10.1021/acs.biomac.9b01282,10.3390/molecules24203678,10.1016/j.cclet.2019.04.008,10.1039/c9dt00455f,10.1080/00958972.2019.1590562,10.1021/acscatal.9b00744,10.1039/c9ra00749k,10.1016/j.tet.2018.10.025,10.1002/jhet.3280,10.1039/c8dt01288a,10.1055/s-0036-1589100,10.1021/acs.organomet.7b00642,10.1021/acs.organomet.7b00280,10.1021/acs.organomet.7b00208,10.1039/c6nj03789e,10.1002/adsc.201601105,10.1021/jacs.6b11412,10.1007/s10562-016-1880-9,10.1021/acs.orglett.6b02330,10.1016/j.tet.2016.07.063,10.1002/ajoc.201600319,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1021/acs.orglett.6b01758,10.1007/s10853-016-9800-3,10.1021/acs.joc.5b02667,10.1039/c6ra23004k,10.1002/anie.201505699,10.1002/ejoc.201500987,10.1016/j.tetlet.2015.07.033,10.1021/acscatal.5b01021,10.1016/j.jorganchem.2015.04.019,10.1039/c5ra12742d,10.1039/c4cy01736f,10.1021/ol503061c,10.1021/jo501665e,10.1002/ejoc.201402919,10.1021/ol501600k,10.1007/s11426-014-5138-3,10.1021/jo501291y,10.1248/cpb.c14-00086,10.1021/cr400230c,10.1021/cs4009946,10.1039/c4ra07105k,10.6023/cjoc201307035,10.1039/c3ob41382a,10.1002/asia.201300688,10.1021/ol401021x,10.3184/174751913X13662179283121,10.1002/pola.26573,10.1039/c3cs35521g,10.1002/pola.26340,10.1002/adsc.201200624,10.1002/pola.26273,10.1002/adsc.201200364,10.1021/ol301847m,10.1021/jo301270t,10.1021/ol301615z,10.1021/jo300547v,10.1002/ejoc.201200444,10.1002/ejoc.201200368,10.1021/ol301221p,10.1021/jo301069c,10.1021/ol301436v,10.1021/jo3001194,10.1021/jo2022982,10.1039/c2ob25225b,10.1002/anie.201207428Kelly12/15/2021
318
156FALSEjo202298210.1021/jo2022982https://sci-hub.wf/10.1021/jo2022982https://doi.org/10.1021/jo2022982NiC-O ActivationLongTRUE79141062012Percec, V
Ni(COD)(2)/PCy3 Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates in THF at Room Temperature
JOURNAL OF ORGANIC CHEMISTRY
Reaction conditions for the Ni(COD)(2)/PCy3 catalyzed cross-coupling of aryl neopentylglycolboronates with aryl mesylates were developed. By using optimized reaction conditions, Ni(COD)(2)/PCy3 was shown to be a versatile catalyst for the cross-coupling of a diversity of aryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates containing both electron-donating and electron-withdrawing substituents in their para, ortho, and meta positions in THF at room temperature. This Ni-catalyzed cross-coupling of aryl neopentylglycolboronates is also effective for the synthesis of heterobiaryls and biaryls containing electrophilic functionalities sensitive to organolithium and organomagnesium derivatives. In combination with the recently developed Ni-catalyzed neopentylglycolborylation, all Ni-catalyzed routes to functional biaryls and heterobiaryls are now easily accessible.
Univ Penn1/20/2012TRUETRUEFALSECsp2_ar-Csp2_arE-NuOBOMsB(nep)ArylArylK3PO4Ionic-PO4Weak0.36_xxshihong added10.1021/jo3001194,10.1021/jacs.6b11412,10.1016/j.tet.2012.04.005,10.1002/adsc.201400460,10.1021/ja5029793,10.1021/acs.joc.6b01627,10.1021/om500452c,10.1021/ol503061c,10.1002/anie.201412051,10.1002/ejic.201900692,10.1021/jo300547v,10.1002/ejoc.201200444,10.1021/jo501291y,10.1039/c4qo00321g10.1039/d1ob01619a,10.1055/a-1548-8362,10.1021/acscatal.0c03334,10.1021/acs.chemrev.0c00088,10.1039/d0nj01610a,10.1021/acs.biomac.0c00507,10.1021/acs.biomac.9b01765,10.1021/acs.biomac.9b01282,10.1002/ejic.201900692,10.1039/c9ob00313d,10.1007/3418_2018_19,10.1186/s13065-018-0510-6,10.1016/j.tet.2018.10.025,10.3390/molecules23102435,10.1002/adsc.201800729,10.3390/molecules23071715,10.1002/aoc.4273,10.1055/s-0036-1591523,10.1021/acs.orglett.7b03713,10.1039/c7cy01205e,10.1055/s-0036-1588508,10.1021/acs.joc.7b01566,10.1021/acs.organomet.7b00208,10.1002/adsc.201601105,10.1039/c6nj02887j,10.1021/jacs.6b11412,10.1021/acscatal.6b02964,10.1016/j.jorganchem.2016.09.026,10.1021/acs.joc.6b01627,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1021/acs.orglett.6b01758,10.1002/tcr.201500305,10.1007/s41061-016-0043-1,10.1021/acs.joc.5b02667,10.1016/j.tet.2015.10.011,10.1002/ejoc.201500987,10.1002/ejoc.201500734,10.1055/s-0034-1378867,10.1016/j.tet.2015.02.088,10.1021/acs.joc.5b00771,10.1021/acs.accounts.5b00051,10.1016/j.jorganchem.2015.01.009,10.1002/anie.201412051,10.1021/ol503560e,10.1071/CH15459,10.1039/c4qo00321g,10.1039/c5gc01170a,10.1021/ol503061c,10.1021/om500452c,10.1002/adsc.201400460,10.1007/s11426-014-5138-3,10.1021/jo501291y,10.1002/adsc.201400201,10.1021/ja5029793,10.1021/ol500675q,10.1021/cs4009946,10.1021/ja410883p,10.1039/c4cc05151c,10.6023/cjoc201307035,10.1039/c4ra05999a,10.1039/c3ob41382a,10.1002/asia.201300688,10.1002/aoc.3000,10.1002/pola.26573,10.1039/c3cs35521g,10.1002/ejoc.201201061,10.1002/adsc.201200364,10.1021/jo301270t,10.1021/ol301615z,10.1021/jo300547v,10.1002/ejoc.201200444,10.1002/ejoc.201200368,10.1016/j.tet.2012.04.005,10.1021/ol300671y,10.1021/jo202472k,10.1021/jo3001194Kelly11/9/2021
319
336FALSEja301382510.1021/ja3013825https://sci-hub.wf/10.1021/ja3013825https://doi.org/10.1021/ja3013825NiC-N ActivationLong17-FebTRUE8611452012Doyle, AG
Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines
J AM CHEM SOC
A nickel-catalyzed cross-coupling reaction between N-sulfonyl aziridines and organozinc reagents is reported. The catalytic system comprises an inexpensive and air-stable Ni(II) source and dimethyl fumarate as ligand. Regioselective synthesis of beta-substituted amines is possible under mild and functional-group-tolerant conditions. The stereoselectivity of the reaction is consistent with a stereoconvergent mechanism wherein the sulfonamide directs C-C bond formation.
Princeton Univ6/13/2012TRUETRUEFALSECsp3-Csp3E-NuNZn
N(Ring-Opening)
ZnXAlkylAlkylNo baseNo Base_x10.1055/s-0037-1610084,10.1021/ja505823s,10.1021/jacs.5b02503,10.1039/c9cc08079a,10.1021/acs.orglett.9b01014,10.1021/ja3089422,10.1021/acs.orglett.8b01062,10.1021/jacs.9b00111,10.1021/jacs.7b02389,10.1038/ncomms12937,10.1021/jacs.7b0344810.1039/d2cc00461e,10.1039/d1sc05451a,10.3390/molecules26195947,10.1021/acs.orglett.1c02514,10.1016/j.jorganchem.2021.122068,10.1021/jacs.1c05281,10.1021/acs.orglett.1c01821,10.1039/d1qo00458a,10.1021/acs.orglett.1c01077,10.1002/adsc.202100195,10.1021/acs.organomet.0c00775,10.1039/d0cs01107j,10.1021/jacs.1c01916,10.1039/d0qo01479f,10.1021/acs.accounts.0c00694,10.1055/a-1344-6040,10.1055/a-1344-2434,10.1021/acs.oprd.0c00367,10.1021/acs.organomet.0c00242,10.1021/acscatal.0c03341,10.1021/acscatal.0c03334,10.1002/cctc.202000597,10.1021/acs.joc.0c00530,10.1039/d0ob00535e,10.1021/acscatal.0c01199,10.1021/jacs.0c02237,10.1002/anie.201915454,10.1021/jacs.0c01724,10.1021/acs.orglett.0c00554,10.1002/chem.202000215,10.1038/s41467-019-14016-1,10.1039/c9cc08079a,10.1021/acscatal.9b04823,10.1016/j.trechm.2019.08.004,10.1002/anie.201910168,10.1039/c9sc02507c,10.1039/c9cc05385a,10.1039/c9cc04795f,10.1021/acscatal.9b01347,10.1021/acscombsci.9b00076,10.1021/jacs.9b05934,10.1002/chem.201902009,10.1039/c9qo00320g,10.1021/acscatal.9b01620,10.1002/chem.201901128,10.1021/acscatal.9b01191,10.1021/acs.orglett.9b01014,10.1021/jacs.9b00111,10.1016/j.tetlet.2018.12.027,10.1021/acs.organomet.8b00720,10.1021/acsomega.8b03019,10.1021/jacs.8b11942,10.1039/c8cc07093h,10.2533/chimia.2018.595,10.1055/s-0037-1610084,10.1021/acs.orglett.8b01394,10.1002/anie.201802347,10.1016/j.isci.2018.04.020,10.1021/acs.orglett.8b01062,10.1021/acs.joc.8b00402,10.1021/acs.orglett.7b03747,10.1039/c8ra09048c,10.1080/00397911.2018.1471509,10.6023/cjoc201702033,10.1002/anie.201707673,10.1021/jacs.7b06723,10.1021/acs.orglett.7b01886,10.1002/chem.201702200,10.1021/jacs.7b06288,10.1002/pola.28519,10.1021/jacs.7b03448,10.1021/jacs.7b02389,10.1021/acs.orglett.7b00447,10.1021/acs.orglett.7b00504,10.1039/c6gc03144g,10.1021/acs.orglett.6b03430,10.1039/c6cs00150e,10.1021/acs.orglett.6b02253,10.1016/j.tetlet.2016.07.080,10.1038/ncomms12937,10.1021/jacs.6b06285,10.1021/acscatal.5b02718,10.1002/adsc.201500903,10.2174/1385272819666150423202719,10.1039/c5nj01833a,10.1039/c5ob02121a,10.1039/c5gc01323b,10.1039/c6cc04410g,10.1039/c6sc01120a,10.1021/acs.joc.5b02557,10.1002/chem.201504049,10.1021/jacs.5b07397,10.1021/acs.chemrev.5b00386,10.1021/acs.joc.5b01931,10.1021/acs.chemrev.5b00162,10.1016/j.tet.2015.06.013,10.1016/j.jorganchem.2015.05.051,10.1016/j.tet.2015.05.098,10.1002/adsc.201400850,10.1002/chem.201500886,10.1021/jacs.5b02503,10.1021/acs.accounts.5b00064,10.1055/s-0034-1380141,10.1021/jacs.5b00473,10.1021/ja511335v,10.1039/c4cc09321f,10.1016/S1872-2067(14)60217-5,10.1002/adsc.201400476,10.1021/cr500036t,10.1021/ja505823s,10.1021/ja5039616,10.1021/ol501024y,10.1038/nature13274,10.1021/om5001327,10.1002/adsc.201400049,10.1021/ja410686v,10.1002/chem.201302421,10.1002/adsc.201300454,10.1021/ja4076716,10.1007/s11426-013-4880-2,10.1007/s40242-013-3057-z,10.1021/ja400325w,10.1021/om301263s,10.1021/ja3089422,10.1002/anie.201209887,10.1055/s-0031-1290467,10.1002/anie.20120463312/22/2021JUN 132012FALSEFALSEFALSEFALSE134239541
320
337FALSEja208208710.1021/ja2082087https://sci-hub.wf/10.1021/ja2082087https://doi.org/10.1021/ja2082087NiC-H ActivationGerryTRUE132161422011Hartwig, JF
Nickel-Catalyzed Asymmetric alpha-Arylation and Heteroarylation of Ketones with Chloroarenes: Effect of Halide on Selectivity, Oxidation State, and Room-Temperature Reactions
J AM CHEM SOC
We report the alpha-arylation of ketones with a range of aryl chlorides with enantioselectivities from 90 to 99% ee catalyzed by the combination of Ni(COD)(2) and (R)-BINAP and the coupling of ketones with a range of heteroaryl chlorides with enantioselectivities up to 99% ee catalyzed by Ni(COD)(2) and (R)-DIFLUORPHOS. The analogous reactions of bromoarenes occur with much lower enantioselectivities. Mechanistic studies showed that the difference in the rates of decomposition of the arylnickel(II) halide intermediates to {[(R)-BINAP]NiX}(2) likely accounts for the difference in the enantioselectivities of the reactions of bromoarenes and chloroarenes. This catalyst decomposition can be overcome by conducting the reactions with [(R)-BINAP]Ni(eta(2)-NC-Ph) (4), which undergoes oxidative addition to haloarenes at room temperature.
Univ Illinois10/19/2011Csp3-Csp2_arE-NuHXHClAlkylArylIonic-OtBuNu-H_10.1039/c5sc03704b,10.1021/jacs.1c06614,10.1039/c4cc00716f,10.1021/acscatal.0c00393,10.1039/c5sc01589h,10.1002/anie.202006826,10.1021/ol403209k,10.1021/jacs.5b02945,10.1021/acscatal.6b00865,10.1039/c4cc00959b,10.1039/c6ob01299j,10.1021/jacs.7b06191,10.1002/anie.201403823,10.1002/anie.201412051,10.1002/chem.201406457,10.1021/acscatal.6b0036510.1039/d1qo01765a,10.1002/ejic.202101013,10.1038/s41467-021-27028-7,10.1021/acs.orglett.1c02093,10.1021/acs.organomet.1c00325,10.1021/jacs.1c06614,10.1055/a-1560-5245,10.1002/anie.202106109,10.1021/jacs.1c05281,10.1016/j.tetlet.2021.153208,10.1039/d1sc01217g,10.1055/a-1503-7339,10.1016/j.ica.2021.120300,10.1002/anie.202101668,10.1016/j.chempr.2021.02.013,10.1021/jacs.0c13236,10.2174/1385272825666210531110403,10.1002/asia.202001032,10.1021/acs.orglett.0c02913,10.1039/d0qo00447b,10.1021/acs.joc.0c01768,10.1002/anie.202006826,10.1021/acs.chemrev.9b00682,10.1021/acscatal.0c02414,10.1021/acs.orglett.0c01129,10.1021/acscatal.0c00393,10.1021/jacs.0c00783,10.1002/ejoc.202000169,10.1021/acs.orglett.0c00485,10.3791/60441,10.1021/acscatal.9b04480,10.1021/acs.organomet.9b00672,10.1021/acs.joc.9b00446,10.1021/acs.orglett.9b01373,10.1021/acs.orglett.9b01628,10.1021/acscatal.8b04357,10.1021/acs.orglett.9b00294,10.1021/acscatal.8b05025,10.1039/c8nj05503c,10.1002/anie.201808509,10.1021/acs.organomet.8b00438,10.1002/anie.201807302,10.1039/c8qo00510a,10.1002/adsc.201800724,10.1002/anie.201804318,10.1039/c8sc00827b,10.1021/acs.inorgchem.7b02546,10.1039/c7qo00934h,10.1002/anie.201709411,10.1021/jacs.7b10365,10.1021/acs.orglett.7b02012,10.1002/anie.201705321,10.1021/jacs.7b06191,10.1021/acs.orglett.7b00761,10.1021/acs.orglett.7b00428,10.1021/acscatal.6b03355,10.1039/c6cc08392g,10.1021/jacs.6b11610,10.1021/jacs.6b09580,10.1002/adsc.201600587,10.1021/acs.organomet.6b00484,10.1002/tcr.201500305,10.1021/jacs.6b02120,10.1021/acscatal.6b00865,10.1021/jacs.6b01214,10.1002/anie.201511487,10.1021/acscatal.6b00365,10.3987/COM-15-S(T)21,10.1002/anie.201510638,10.1002/anie.201510558,10.1039/c6ob01299j,10.2174/1385272819666150423202719,10.1039/c5sc03704b,10.1039/c5qo00334b,10.1021/acs.organomet.5b00733,10.1002/ejoc.201500734,10.1021/jacs.5b02945,10.1038/ncomms8011,10.1021/jacs.5b00538,10.1002/anie.201412051,10.1002/anie.201500404,10.1002/chem.201406457,10.1039/c5ob01203a,10.1039/c5sc01589h,10.1002/chem.201405246,10.1021/ma5009429,10.1002/chem.201403446,10.1002/adsc.201400201,10.1002/anie.201403823,10.1021/om500156q,10.1021/ol5005565,10.1021/cr4003243,10.1021/ol500292c,10.1021/ja411911s,10.1039/c3ob42050g,10.1021/ja410650e,10.1021/ol403209k,10.1039/c4cc00716f,10.1039/c4cc00959b,10.1039/c4qo00027g,10.1002/chem.201303384,10.1021/ol4029447,10.1021/ol402336u,10.1021/ma401314x,10.1021/om400711d,10.1002/anie.201303602,10.1021/ol401416r,10.1021/ja402922w,10.1016/j.tet.2012.12.002,10.1002/chem.201202798,10.1039/c3sc50806d,10.1002/anie.201300621,10.1002/anie.201300481,10.1039/c3sc00090g,10.1021/ja306602g,10.1021/jo301984p,10.1055/s-0032-1316738,10.1002/ejoc.201101648,10.1039/c2cc36452b,10.1002/anie.201207428,10.1070/RC2012v081n09ABEH004305,10.1055/s-0031-12901112/16/2022
321
133FALSEjo300119410.1021/jo3001194https://sci-hub.wf/10.1021/jo3001194https://doi.org/10.1021/jo3001194NiC-O ActivationElaineTRUE67111062012Percec, V
Nickel Catalyzed Cross-Coupling of Aryl C-O Based Electrophiles with Aryl Neopentylglycolboronates
JOURNAL OF ORGANIC CHEMISTRY
The efficiency of mesylates, sulfamates, esters, carbonates, carbamates, and methyl ethers as C-O-based electrophiles attached to the 1- or 2-position of naphthalene and to activated and nonactivated phenyl substrates was compared for the first time in Ni-catalyzed cross-coupling with phenyl neopentylglycolboronates containing electron-rich and electron-deficient substituents in their para-position. These experiments were performed in the presence of four different Ni(II)- and Ni(0)-based catalysts. Ni(II)-based catalysts mediate the cross-coupling of most 2-naphthyl C-O electrophiles with both arylboronic acids and with neopentylglycolboronates when K3PO4 is used as base. The same catalysts are not efficient when CsF is used as base. However, Ni(0)-based catalysts exhibit selective efficiency, and when reactive, their efficiency is higher than that of Ni(II)-based catalysts in the presence of both K3PO4 and CsF. These results provide both reaction conditions for the cross-coupling, and for the elaboration of orthogonal cross-coupling methodologies of various C-O based electrophiles with aryl neopentylglycolboronates. With the exception of mesylates and sulfamates the efficiency of all other 2-naphthyl C-O electrophiles was lower in cross-coupling with aryl neopentylglycolboronates than with arylboronic acids
Univ Penn3/16/2012YCsp2_ar-Csp2_arE-NuOBOMsB(nep)ArylArylK3PO4Ionic-PO4Weak0.36TM10.1039/c4qo00321g,10.1021/om500452c,10.1002/adsc.201400460,10.1021/jo300547v,10.1021/jacs.6b11412,10.1021/ol403209k,10.1021/acscatal.9b00744,10.1021/jo4005537,10.1021/jo501291y,10.1021/ol503061c,10.1021/jacs.7b0497310.1055/a-1548-8362,10.17344/acsi.2021.6920,10.1021/acs.joc.0c02209,10.1016/j.tetlet.2020.152605,10.1021/acscatal.0c03334,10.1021/acs.biomac.9b01765,10.1021/acs.biomac.9b01282,10.1021/acscatal.9b00744,10.1021/acs.orglett.9b00294,10.1039/c8nj05503c,10.1016/j.tet.2018.10.025,10.1021/acs.organomet.8b00589,10.1002/chem.201706102,10.1039/c8dt01288a,10.1016/j.jorganchem.2018.01.019,10.1002/aoc.4273,10.1055/s-0036-1591523,10.1007/s40242-017-6455-9,10.1021/jacs.7b04973,10.1002/ejic.201700057,10.1002/adsc.201601105,10.1038/s41570-017-0025,10.1021/jacs.6b11412,10.1021/acs.orglett.6b02330,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1021/acs.orglett.6b01758,10.1021/acs.macromol.6b01006,10.1021/acs.joc.6b00767,10.1021/acs.joc.5b02667,10.1016/j.apcata.2015.11.044,10.1002/anie.201505699,10.1002/ejoc.201500987,10.1016/j.jorganchem.2015.04.019,10.6023/cjoc201408028,10.1039/c4qo00321g,10.1039/c5ra09765g,10.1016/j.tetlet.2014.11.020,10.1021/ol503061c,10.1016/j.catcom.2014.08.010,10.1016/j.tet.2014.08.035,10.1021/om500452c,10.1002/adsc.201400460,10.1007/s11426-014-5138-3,10.1021/jo501291y,10.1016/j.tet.2014.04.059,10.1021/om5001327,10.1021/jo500675a,10.1021/om500156q,10.1021/cs4009946,10.1021/ol403209k,10.6023/cjoc201307035,10.1039/c3ob41382a,10.1002/asia.201300688,10.1002/aoc.3000,10.1021/jo4005537,10.1002/pola.26573,10.1021/ja3116718,10.1039/c3cs35521g,10.1002/pola.26340,10.1021/jo301270t,10.1021/ol301615z,10.1021/jo300547v,10.1002/anie.201207428Kelly12/16/2021
322
147FALSEjo300547v10.1021/jo300547vhttps://sci-hub.wf/10.1021/jo300547vhttps://doi.org/10.1021/jo300547vNiC-O ActivationLongTRUE75101062012Percec, V
trans-Chloro(1-Naphthyl)bis(triphenylphosphine)nickel(II)/PCy3 Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates at Room Temperature
JOURNAL OF ORGANIC CHEMISTRY
trans-Chloro(1-naphthyl)bis(triphenylphosphine)nickel-(II) complex/PCy3 system has been successfully applied as catalyst for the Suzuki-Miyaura cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature. This cross-coupling reaction tolerates various functional groups, including keto, imino, ester, ether, and cyano. Together with the nickel-catalyzed, one-pot, two-step neopentylglycolborylation, this bench stable and inexpensive Ni(II)-based catalyst can be utilized as an alternative to Ni(COD)(2)/PCy3 to provide an inexpensive, robust, and convenient synthesis of biaryl and heterobiaryl compounds.
Univ Penn7/20/2012Csp2_ar-Csp2_arE-NuOBOMsB(OH)2ArylArylK3PO4Ionic-PO4Weak0.36_10.1021/ol503061c,10.1021/jacs.6b11412,10.1021/om500452c,10.1021/ol401727y,10.1021/jacs.1c08502,10.1039/c7cc06717h,10.1021/cs501045v,10.1021/ol301847m,10.1039/c4qo00321g,10.1021/jo501291y10.1002/chem.202104230,10.1021/jacs.1c08502,10.1002/ijch.202100057,10.1039/d1nj03706d,10.1021/acscatal.0c03334,10.1016/j.tetlet.2020.151940,10.1021/acs.joc.0c00178,10.1021/acs.biomac.9b01765,10.1021/jacs.0c02075,10.1002/ejoc.201901730,10.1021/acscatal.9b04353,10.1021/acs.biomac.9b01282,10.1021/jacs.9b08961,10.1039/c9dt00455f,10.1039/c9ob00313d,10.1021/acs.orglett.9b00294,10.1016/j.tet.2019.01.015,10.1039/c8nj05503c,10.1016/j.tet.2018.10.025,10.3390/molecules23102435,10.1039/c8ob01034j,10.1039/c8dt01288a,10.1002/ajoc.201700681,10.1055/s-0036-1591888,10.1246/cl.170907,10.1039/c7cc06717h,10.1021/acs.organomet.7b00726,10.1021/acs.oprd.7b00253,10.1016/j.tetasy.2017.03.008,10.1039/c6nj03789e,10.1021/jacs.6b11412,10.1007/s10562-016-1880-9,10.1021/acs.orglett.6b02330,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1021/acs.orglett.6b01758,10.1021/acs.joc.6b01041,10.1055/s-0035-1561302,10.1039/c6cc00536e,10.1039/c6ra23004k,10.1002/ejoc.201500987,10.1021/acs.joc.5b01253,10.1021/acs.orglett.5b01466,10.1055/s-0034-1378691,10.1016/j.jorganchem.2015.01.009,10.1016/j.tet.2015.01.008,10.1021/jo502446k,10.1021/ol503560e,10.1039/c4qo00321g,10.1039/c4cy01736f,10.1021/ol503061c,10.1021/om500452c,10.1021/cs501045v,10.1021/jo501291y,10.1016/j.tet.2014.04.059,10.1002/chem.201402487,10.1021/ol500675q,10.1002/ejoc.201400090,10.1021/om500156q,10.1021/cs4009946,10.6023/cjoc201307035,10.1039/c3dt52412d,10.1039/c3cs60197h,10.1002/chem.201302621,10.1039/c3ob41382a,10.1002/asia.201300688,10.1021/ol401727y,10.1002/aoc.3000,10.1002/pola.26573,10.1021/ja3116718,10.1039/c3cs35521g,10.1021/ol301847mKelly12/15/2021
323
341FALSEanie.20045416610.1002/anie.200454166https://sci-hub.wf/10.1002/anie.200454166https://doi.org/10.1002/anie.200454166NiC-H ActivationElaine14-FebTRUE1353#N/A2004Cavell, KJ
Transition-metal-catalyzed reactions involving imidazolium salt/N-heterocyclic carbene couples as substrates
ANGEW CHEM INT EDIT
Cardiff Univ7/12/2004FALSEFALSEFALSEYCsp2_ar-Csp2Nu-NuHHHHHetVinylNo baseNo BaseNu-H_10.1021/ja401344e,10.1021/ol9001587,10.1021/ja413131m10.1016/j.mtsust.2021.100102,10.1039/d1cc07309e,10.1021/acs.organomet.1c00350,10.1016/j.ccr.2021.213860,10.1016/bs.adomc.2021.01.006,10.1039/d0ob01453b,10.1039/d0cp04080k,10.6023/cjoc202005050,10.1039/d0sc02629h,10.1016/j.chempr.2020.04.005,10.1021/acs.inorgchem.0c00355,10.1039/d0nj00311e,10.1039/c9cs00539k,10.1039/c9ra05605j,10.1002/chem.201903242,10.1021/acs.orglett.9b01645,10.1002/ejic.201900484,10.1002/anie.201806631,10.1021/acs.chemrev.8b00505,10.3866/PKU.WHXB201809036,10.1021/jacs.8b09677,10.1002/cjoc.201800314,10.1021/jacs.8b02547,10.1002/ejoc.201701509,10.1002/adsc.201701515,10.1039/c7cy02409f,10.1016/j.apsusc.2017.08.019,10.1039/c7dt03099a,10.1039/c7qo00331e,10.1021/acs.chemrev.6b00574,10.1021/acs.chemrev.6b00594,10.1039/c7cc01076a,10.1021/acscatal.6b02477,10.1055/s-0035-1561604,10.1002/cctc.201501086,10.1007/3418_2015_117,10.1016/j.tet.2015.05.004,10.1016/j.tet.2015.03.066,10.1246/cl.150024,10.1021/acscatal.5b00243,10.1002/chem.201405923,10.1002/cctc.201402943,10.1021/om501275c,10.1039/c5ob00823a,10.1039/c5dt00032g,10.1007/s10562-014-1451-x,10.1021/om500369g,10.1002/chem.201400303,10.1021/ja413131m,10.1080/00958972.2014.911291,10.1002/cctc.201300339,10.1021/ol402644y,10.1021/ja401344e,10.6023/cjoc201208032,10.1002/chem.201203201,10.1039/c3cy20796j,10.1021/ol301606y,10.1021/ol300570f,10.1016/j.comptc.2012.02.014,10.1039/c2nj40287d,10.1039/c1cc14593b,10.1021/ja206850s,10.1002/tcr.201100023,10.1055/s-0030-1260799,10.1002/cctc.201000321,10.1021/ol102643a,10.1021/ja107342b,10.1039/c0ob00669f,10.1021/om1008499,10.1021/om100684a,10.1055/s-0029-1218837,10.1021/jo100228u,10.1002/adsc.201000144,10.1021/cr900005n,10.1002/anie.201001849,10.1007/128_2009_12,10.1002/chem.200902929,10.1039/c0dt00104j,10.1007/978-3-642-04722-0_4,10.1002/cctc.200900127,10.1055/s-0029-1217747,10.1021/om900398h,10.1021/jo901350j,10.1016/j.tetlet.2009.02.195,10.1021/ol9001587,10.1002/chem.200900373,10.1039/b815876b,10.1021/ol802572n,10.1021/om800455h,10.1021/om8008052,10.1021/ja807258m,10.1021/om800472v,10.1021/om8003948,10.1021/ar800042p,10.1021/om800140n,10.1021/om8000839,10.1021/ma702505n,10.1021/om701151g,10.1021/om700977f,10.1002/anie.200703883,10.1039/b811449h,10.2516/ogst:2007070,10.1021/om070181e,10.1016/j.ccr.2006.08.016,10.1021/ic062368o,10.1021/ja067112w,10.1002/anie.200603907,10.1002/anie.200703758,10.1135/cccc20070609,10.1039/b709914b,10.1016/j.jorganchem.2006.07.013,10.1021/om060439l,10.1021/ja0623459,10.1021/ja058253l,10.1021/jo052345b,10.1021/om051004l,10.1021/ja0576684,10.1021/om050849u,10.1002/aoc.1008,10.1039/b602046a,10.1021/om050600c,10.1002/anie.200500884,10.1021/jo048666p12/15/20212004FALSEFALSEFALSEFALSE43293845
324
145FALSEjo302086g10.1021/jo302086ghttps://sci-hub.wf/10.1021/jo302086ghttps://doi.org/10.1021/jo302086gNiC-O ActivationGerryTRUE8110382012Weix, DJ
Comparison of Arylboron-Based Nucleophiles in Ni-Catalyzed Suzuki-Miyaura Cross-Coupling with Aryl Mesylates and Sulfamates
JOURNAL OF ORGANIC CHEMISTRY
The efficiency of arylboron-based nucleophiles, boronic acid, potassium trifluoroborate, neopentylglycolboronate, and pinacol boronate in nickel-catalyzed Suzuki-Miyaura cross-coupling reactions with the two C-O electrophiles, mesylates, and sulfamates was compared. Arylboronic acid is the most reactive and most atom-economic of the four boron species studied. Arylpotassium trifluoroborate cross-couples efficiently only in the presence of water. la the absence of water, aryl neopentylglycolboronate is more efficient, less expensive, and more atom-economic than aryl pinacolboronate.
Univ Rochester11/16/2012yCsp3-Csp2_arE-EOXOAcXAllylArylNo baseNo BaseMedium0.31_10.1021/jacs.0c13093,10.1039/c7sc03140h,10.1002/anie.201705521,10.1021/ja5029793,10.1039/c3ob40232k,10.1002/chem.201601320,10.1021/jacs.9b05224,10.1002/anie.201601206,10.1039/c8sc00609a,10.1039/c5cc03113c10.1055/s-0041-1737762,10.1002/chem.202103643,10.1002/ejic.202100820,10.1039/d1ob01874d,10.1021/acs.orglett.1c02893,10.1021/jacs.1c08695,10.1021/acs.orglett.1c02616,10.1039/d1sc04011a,10.1021/jacs.1c04254,10.1002/tcr.202100142,10.1021/acs.orglett.1c00812,10.6023/cjoc202008012,10.1021/jacs.0c13093,10.1021/acscatal.0c02454,10.1039/c9cc07072a,10.1002/anie.201909543,10.1021/jacs.9b05224,10.1021/acs.orglett.9b01987,10.1039/c9cc03344k,10.1021/acs.orglett.9b01019,10.6023/cjoc201806038,10.1002/anie.201805118,10.1039/c8sc00609a,10.1055/s-0037-1609093,10.1055/s-0036-1591853,10.1039/c7sc03140h,10.1002/anie.201705521,10.1002/anie.201706781,10.1002/cjoc.201700071,10.1021/acs.orglett.7b01208,10.1002/anie.201702857,10.1002/anie.201703174,10.1021/acs.joc.6b02830,10.1002/chem.201603832,10.1038/NCHEM.2587,10.1002/adsc.201600568,10.1055/s-0035-1562442,10.1021/acs.orglett.6b01837,10.1002/anie.201604406,10.1007/s41061-016-0042-2,10.1021/acs.orglett.6b01134,10.1126/science.aaf6635,10.1002/anie.201601206,10.1002/chem.201601320,10.1021/acs.joc.5b02151,10.1055/s-0035-1560324,10.1055/s-0035-1560531,10.1021/jacs.5b06255,10.1021/jacs.5b03870,10.1016/j.tet.2014.12.045,10.1039/c4cc08703h,10.1039/c5cc03113c,10.1039/c5qo00224a,10.1021/ja509077a,10.1021/jo501925s,10.1021/om5004682,10.1021/ja508067c,10.1055/s-0033-1339126,10.1002/chem.201402509,10.1021/jo500507s,10.1002/chem.201402302,10.1021/ja5029793,10.1055/s-0033-1340151,10.1039/c3ra47813k,10.1016/j.tetlet.2013.08.049,10.1016/j.tet.2013.05.060,10.1021/ja402922w,10.3762/bjoc.9.81,10.1021/ja309176h,10.1039/c3ob40232kKelly1/19/2022
325
343FALSEanie.20110068310.1002/anie.201100683https://sci-hub.wf/10.1002/anie.201100683https://doi.org/10.1002/anie.201100683NiC-N ActivationKellyTRUE1382052011Wang, ZX
Nickel-Catalyzed Cross-Coupling of Aryltrimethylammonium Iodides with Organozinc Reagents
ANGEW CHEM INT EDIT
Univ Sci & Technol China
4/27/2011FALSEFALSEFALSECsp2_ar-Csp2_arE-NuNZn
NMe3+I-
ZnXArylArylNo baseNo BaseE-H_x10.1021/jo300209d,10.1021/jacs.9b05224,10.1039/c6ob01299j,10.1016/j.tet.2017.06.004,10.1002/chem.201602202,10.1055/s-0036-1588845,10.1002/ajoc.201700569,10.1021/ja3089422,10.1021/om500452c,10.1039/c3ob41989d,10.1021/acscatal.7b01058,10.1039/c4qo00321g,10.1038/ncomms12937,10.1021/jacs.8b08779,10.1039/c2dt30886j,10.1021/ja2084509,10.1021/acs.orglett.9b00242,10.1021/acs.orglett.6b02952,10.1002/chem.201603436,10.1002/anie.20151119710.1021/acs.orglett.1c03590,10.1039/d1ob01690c,10.1016/j.tet.2021.132431,10.1016/j.jorganchem.2021.122073,10.1039/d1ob01468d,10.1021/acs.joc.1c01339,10.1039/d1gc01907d,10.1039/c9cs00571d,10.1039/d1qo00759a,10.1039/d1cc01734a,10.1039/d1sc00757b,10.1016/j.mcat.2021.111500,10.1021/acs.joc.0c02992,10.1021/acs.orglett.0c03660,10.1055/a-1326-6973,10.1021/acscatal.0c03341,10.1002/adsc.202000821,10.1016/j.jorganchem.2020.121354,10.1021/acs.orglett.0c01869,10.1016/j.tetlet.2020.151975,10.1039/d0qo00173b,10.1002/ajoc.202000139,10.1002/cjoc.201900468,10.1002/chem.202000412,10.1021/acs.joc.9b02771,10.1039/c9ob02667c,10.1002/ajoc.201900759,10.1039/c9qo01177c,10.1021/acs.joc.9b02554,10.1039/c9qo01033e,10.1039/c9sc01966a,10.1021/acs.joc.9b01877,10.1039/c9cc05099j,10.1021/acs.orglett.9b02820,10.1016/j.tet.2019.07.007,10.1021/jacs.9b05224,10.1021/acs.oprd.9b00194,10.1016/j.isci.2019.04.038,10.1039/c9sc01083a,10.1002/chem.201900886,10.1021/acscatal.9b00218,10.1021/acs.orglett.9b00499,10.1021/acs.orglett.9b00242,10.1021/acs.joc.8b02926,10.1021/acs.joc.8b02567,10.1021/jacs.8b08792,10.1002/ajoc.201800560,10.1039/c8cc07093h,10.1021/jacs.8b08779,10.1021/acscatal.8b02495,10.6023/cjoc201803013,10.1038/s41467-018-05637-z,10.1002/anie.201804628,10.1039/c8cc03760d,10.1021/acs.joc.8b00965,10.1039/c8ob00488a,10.6023/cjoc201710034,10.1038/s41467-018-03928-z,10.1021/acs.orglett.8b00545,10.1002/anie.201712618,10.1002/cjoc.201700664,10.1055/s-0036-1588548,10.1002/ajoc.201700569,10.1002/ajoc.201700550,10.1002/asia.201701342,10.1055/s-0036-1590893,10.1039/c7gc02775c,10.1002/ijch.201700044,10.1021/jacs.7b08579,10.1002/asia.201701132,10.1002/ajoc.201700242,10.1039/c7sc02181j,10.1055/s-0036-1588845,10.1016/j.tet.2017.06.004,10.1002/asia.201700313,10.1039/c7qo00174f,10.1021/jacs.7b05273,10.1021/acscatal.7b01058,10.6023/cjoc201612014,10.1039/c6sc05705e,10.1021/acs.orglett.7b00447,10.1039/c6qo00670a,10.1039/c6cc08701a,10.1039/c7ra02549a,10.1016/j.tet.2016.10.018,10.1021/acs.orglett.6b02952,10.1002/chem.201603436,10.1021/jacs.6b08164,10.1038/ncomms12937,10.1002/adsc.201600590,10.1002/chem.201602202,10.1002/anie.201600400,10.1002/anie.201600697,10.1002/anie.201511197,10.1039/c6cc06089g,10.1039/c6ob01299j,10.1039/c6cc04531f,10.1039/c5cs00534e,10.1021/acs.joc.5b02557,10.1039/c6ob01038e,10.1002/anie.201507776,10.1002/chem.201503596,10.1021/acs.chemrev.5b00386,10.1002/anie.201508161,10.1021/acs.orglett.5b02458,10.1021/acs.orglett.5b02209,10.1002/chem.201500192,10.3998/ark.5550190.p009.180,10.1039/c4qo00321g,10.1039/c4ra13848a,10.1021/om500452c,10.1021/ol501180q,10.1021/jo500619f,10.1021/ja501649a,10.1002/chem.201303809,10.1039/c3ob41989d,10.1039/c4ob01041h,10.1016/j.tet.2013.09.039,10.1016/j.catcom.2013.07.023,10.1016/j.jorganchem.2013.06.001,10.5059/yukigoseikyokaishi.71.588,10.1016/j.tet.2013.01.053,10.1021/om3011855,10.1021/ja3089422,10.1021/ja310848x,10.1002/ejoc.201201345,10.1002/ejic.201200758,10.1002/adsc.201200369,10.1021/jo300209d,10.1021/ja2084509,10.1039/c2dt30886j11/2/20212011FALSEFALSEFALSEFALSE50214901
326
95FALSEjo400553710.1021/jo4005537https://sci-hub.wf/10.1021/jo4005537https://doi.org/10.1021/jo4005537NiC-O ActivationShihongTRUE50622013Jin, Z
Selective Cross-Coupling of Organic Halides with Allylic Acetates
JOURNAL OF ORGANIC CHEMISTRY
A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.
Nankai Univ5/17/2013Csp2_ar-Csp2_arE-NuOBODMTB(OH)2ArylArylK3PO4Ionic-PO4Strong-0.32TM10.1021/jacs.8b13403,10.1002/adsc.201400460,10.1021/acscatal.9b00744,10.1021/jacs.6b11412,10.1021/jacs.0c06995,10.1021/ol401727y10.1039/d1ta07422a,10.1016/j.jorganchem.2021.122147,10.1055/a-1503-6330,10.1021/acs.joc.0c02389,10.1055/a-1349-3543,10.1080/14756366.2021.1900165,10.1021/jacs.0c06995,10.1016/j.isci.2020.101377,10.1002/aoc.5662,10.1021/acsomega.9b04450,10.1039/c9ob00313d,10.1021/acscatal.9b00744,10.1016/j.ejmech.2019.02.002,10.1055/s-0037-1611720,10.1021/jacs.8b13403,10.1021/acs.joc.8b02104,10.1002/aoc.4273,10.1055/s-0036-1588508,10.1021/acs.joc.7b02004,10.1021/acs.organomet.7b00314,10.3762/bjoc.13.146,10.1021/jacs.6b11412,10.1007/s10562-016-1880-9,10.1016/j.tet.2016.10.018,10.1002/adsc.201600336,10.1002/adsc.201600024,10.1021/acs.joc.5b02667,10.1080/00397911.2016.1192651,10.1039/c5nj01833a,10.1016/j.jorganchem.2015.04.019,10.1021/acs.orglett.5b01466,10.1002/aoc.3312,10.3390/molecules20057528,10.1016/j.jorganchem.2015.01.009,10.3390/catal5010018,10.1021/ja511622e,10.1021/ol503560e,10.1039/c5ra06753g,10.1016/j.tetlet.2014.11.020,10.1002/adsc.201400460,10.1002/chem.201404380,10.1007/s11426-014-5138-3,10.1016/j.tet.2014.04.059,10.1021/cs4009946,10.1039/c4ob00677a,10.6023/cjoc201307035,10.1080/07328303.2013.816851,10.1021/ol401727y12/22/2021
327
55FALSEjo501291y10.1021/jo501291yhttps://sci-hub.wf/10.1021/jo501291yhttps://doi.org/10.1021/jo501291yNiC-O ActivationElaineTRUE363202014Zou, G
Nickel-Catalyzed Suzuki-Miyaura Coupling of Heteroaryl Ethers with Arylboronic Acids
JOURNAL OF ORGANIC CHEMISTRY
Nickel-catalyzed Suzuki-Miyaura coupling of heteroaryl ethers with arylboronic acids was described. Selective activation of the phenol C-O bonds was achieved by converting them into the corresponding aryl 2,4-dimethoxy-1,3,5-triazine-6-yl ethers, in which aryl C-O bond could be selectively cleaved with inexpensive, air-stable NiCl2(dppf) as a catalyst. Coupling of these readily accessible heteroaryl ethers proved tolerant of extensive functional groups.
E China Univ Sci & Technol
8/1/2014Csp2_ar-Csp2_arE-NuOB
OSO2NMe2
B(OH)2ArylArylK3PO4 · 3H2OIonic-PO4Weak0.36TM10.1021/jacs.7b04973,10.1021/jacs.6b11412,10.1021/acs.orglett.6b0139810.1039/d1nj03380h,10.17344/acsi.2021.6920,10.1016/j.isci.2020.101377,10.1021/acsomega.9b04450,10.1016/j.tetlet.2019.151491,10.1007/s41061-019-0255-2,10.1016/j.cclet.2019.04.013,10.1002/jhet.3504,10.1039/c8nj05503c,10.1021/acs.joc.8b02766,10.1016/j.tet.2018.10.025,10.1039/c8gc00860d,10.1016/j.tetlet.2018.05.003,10.1016/j.jorganchem.2018.01.019,10.1021/acscatal.8b00230,10.1055/s-0036-1589116,10.1016/j.tet.2017.10.043,10.1021/acs.organomet.7b00642,10.1021/jacs.7b04973,10.1016/j.jorganchem.2017.05.013,10.1002/adsc.201700260,10.1039/c7dt01805c,10.1021/jacs.6b11412,10.1021/acs.orglett.6b02330,10.1016/j.jorganchem.2016.05.017,10.1055/s-0035-1562343,10.1021/acs.orglett.6b01398,10.1021/acs.joc.6b00421,10.1016/j.jorganchem.2016.02.005,10.1039/c5nj01833a,10.1002/ejoc.201500987,10.1016/j.jorganchem.2015.07.009,10.1021/jo502446k,10.1039/c5cc00430f Long 12/16/2021
328
221FALSEjo702255810.1021/jo7022558https://sci-hub.wf/10.1021/jo7022558https://doi.org/10.1021/jo7022558NiC-O ActivationGerryTRUE14217312008Yang, LM
N-Heterocyclic Carbene-Assisted, Bis(phosphine)nickel-Catalyzed Cross-Couplings of Diarylborinic Acids with Aryl Chlorides, Tosylates, and Sulfamates
JOURNAL OF ORGANIC CHEMISTRY
Efficient bis(phosphine)nickel-catalyzed cross-couplings of diarylborinic acids with aryl chlorides, tosylates, and sulfamates have been effected with an assistance of N-heterocyclic carbene (NHC) generated in situ from N,N'-dialkylimidazoliums, e.g., N-butyl-N'-methylimidazolium bromide ([Bmim]Br), in toluene using K3PO4 center dot 3H(2)O as base. In contrast to bis(NHC)nickel-catalyzed conventional Suzuki coupling of arylboronic acids, mono(NHC)bis(phosphine)nickel species generated in situ from Ni(PPh3)(2)Cl-2/[Bmim]Br displayed high catalytic activities in the cross-couplings of diarylborinic acids. The structural influences from diarylborinic acids were found to be rather small, while electronic factors from aryl chlorides, tosylates, and sulfamates affected the couplings remarkably. The couplings of electronically activated aryl chlorides, tosylates, and sulfamates could be efficiently effected with 1.5 mol % NiCl2(PPh3)(2)/[Bmim]Br as catalyst precursor to give the biaryl products in excellent yields, while 3-5 mol % loadings had to be used for the couplings of non- and deactivated ones. A small ortho-substitutent on the aromatic ring of aryl chlorides, tosylates, and sulfamates was tolerable. Applicability of the nickel-catalyzed cross-couplings in practical synthesis of fine chemicals has been demonstrated in process development for a third-generation topical retinoid, Adapalene.
Chinese Acad Sci2/15/2008yCsp2_ar-Nsp3E-NuOHOTsHAryl
Morpholine
NaOtBuIonic-OtBuWeak0.36_xxx10.1021/ol301847m,10.1002/adsc.201100151,10.1002/ejoc.201001519,10.1002/ejoc.201000147,10.1039/c1sc00230a,10.1021/acscatal.8b01879,10.1021/ja200398c,10.1021/acs.orglett.7b00556,10.1021/acscatal.6b00865,10.1021/cs501045v,10.1021/om300566m,10.1021/acs.joc.8b02498,10.1021/ol401727y,10.1021/ol201437g,10.1021/jo3001194,10.1021/ol403209k,10.1002/anie.20100732510.1039/d2ob00330a,10.1002/tcr.202100142,10.1021/acs.organomet.0c00140,10.1055/s-0040-1707356,10.1039/d0nj01610a,10.1134/S1070363220040258,10.1007/s11030-019-10001-4,10.1039/c8nj05503c,10.1021/acs.joc.8b02588,10.1055/s-0037-1610251,10.1021/acs.joc.8b02498,10.1021/acs.organomet.8b00589,10.1021/acs.organomet.8b00567,10.1002/asia.201800575,10.1021/acs.orglett.8b01758,10.1021/acscatal.8b01879,10.1002/aoc.4273,10.1021/acs.orglett.7b03560,10.1021/acscatal.7b03215,10.1007/s10593-018-2220-3,10.1021/acs.joc.7b02363,10.1002/ajoc.201700464,10.1007/s11172-017-1920-7,10.1021/acsomega.7b01165,10.1038/s41570-017-0052,10.1039/c7dt01805c,10.1021/acs.orglett.7b00820,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1002/ajoc.201600535,10.1016/j.cclet.2016.11.002,10.1016/j.jorganchem.2016.12.029,10.1038/s41570-017-0025,10.1039/c6ra27325d,10.1002/adsc.201600950,10.1002/aoc.3527,10.1016/j.tet.2016.08.062,10.1055/s-0035-1562777,10.1007/s00706-016-1673-2,10.1055/s-0035-1562342,10.1002/tcr.201500305,10.1126/science.aag0209,10.1021/acscatal.6b00865,10.1016/j.tet.2016.02.069,10.1002/chem.201503926,10.1021/acscatal.5b02021,10.1039/c5ob02535d,10.1021/acs.oprd.5b00314,10.1002/adsc.201500461,10.1055/s-0035-1560712,10.1016/j.tet.2015.06.103,10.1002/ejoc.201500734,10.1002/hc.21267,10.1021/acs.joc.5b01272,10.1002/ajoc.201500062,10.1055/s-0034-1380141,10.1002/anie.201500404,10.1021/jo5025078,10.1016/j.molcata.2014.10.031,10.1002/ejoc.201402919,10.1021/cs501045v,10.1002/anie.201404355,10.1039/c4cc04111a,10.1002/adsc.201400201,10.1002/ejoc.201402022,10.1021/om500156q,10.1021/om401028d,10.1021/ja411911s,10.1021/ol403209k,10.1039/c4qo00233d,10.1039/c3qo00045a,10.1039/c3ob42053a,10.1039/c3ra46288a,10.1002/adsc.201300485,10.1021/jo4011415,10.1021/ol401727y,10.1002/jhet.1710,10.1016/j.tet.2013.04.073,10.1021/jo400435z,10.1002/ejoc.201201263,10.1021/ja3116718,10.1039/c3ra44195d,10.1021/op300236f,10.1021/ol302688u,10.6023/cjoc201206020,10.1016/j.tetlet.2012.08.015,10.1016/j.tet.2012.07.084,10.1021/om300566m,10.1021/ol3021836,10.1021/ol301847m,10.1016/j.tet.2012.05.054,10.1021/jo301270t,10.1016/j.tetlet.2012.02.081,10.1021/jo3001194,10.1016/j.tet.2011.10.072,10.1039/c2ob25225b,10.1021/ol2024357,10.1246/cl.2011.1254,10.1021/ol202058r,10.1107/S1600536811032326,10.1002/adsc.201100151,10.1016/j.tet.2011.05.057,10.1021/ol201437g,10.1016/j.jorganchem.2011.03.038,10.1021/om200090d,10.1021/ja200398c,10.1055/s-0030-1259728,10.1002/ejoc.201001519,10.1021/cr100259t,10.1021/jo1022052,10.3998/ark.5550190.0012.a10,10.1002/anie.201007325,10.1039/c1sc00230a,10.1002/chem.201002273,10.1016/j.jorganchem.2010.08.047,10.1016/j.tetlet.2010.08.100,10.1002/adsc.201000223,10.1016/S1872-2067(09)60089-9,10.1016/j.tetlet.2010.05.098,10.1055/s-0030-1258080,10.1055/s-0030-1258116,10.1002/ejoc.201000147,10.3184/030823410X12680525004303,10.1016/j.tetlet.2009.10.096,10.1021/cr900074m,10.1016/j.tetlet.2009.03.108,10.1021/ol802493z,10.1039/b819510b,10.1039/b911286c,10.1002/chem.200800858,10.1002/chem.200802018Kelly11/22/2021
329
268FALSEjo982312e10.1021/jo982312ehttps://sci-hub.wf/10.1021/jo982312ehttps://doi.org/10.1021/jo982312eNiC-O ActivationLong9-MarTRUE851711999Cheng, CH
Nickel-catalyzed amination of aryl tosylates
JOURNAL OF ORGANIC CHEMISTRY
[GRAPHICS] The cross-coupling of aryl tosylates with amines and anilines was accomplished by using a Ni-based catalyst system from the combination of Ni(II)-(sigma-aryl) complexes/N-heterocyclic carbenes (NHCs). The feature, scope, and limitation of this reaction are disclosed.
5/14/1999Csp3-Csp2_arE-EOX
O(Ring-Opening)
IAlkylArylNo baseNo BaseWeak1_10.1021/jo051660v10.1039/d1ra06351k,10.1055/a-1672-2260,10.1055/a-1528-1711,10.1002/ejoc.202000672,10.6023/cjoc201912030,10.1021/acs.orglett.0c00900,10.1021/acs.joc.9b02582,10.1002/adsc.201901152,10.1016/j.tetlet.2019.151228,10.1021/acs.joc.9b01957,10.1039/c8qo01403e,10.1039/c8ob02864h,10.1021/acs.joc.8b01396,10.1021/acs.joc.8b00604,10.1016/j.tet.2018.03.029,10.1039/c7qo01064h,10.1055/s-0036-1588692,10.1021/acs.joc.6b03038,10.1055/s-0035-1560565,10.3762/bjoc.12.209,10.1021/acs.joc.6b00667,10.1021/acs.orglett.6b00757,10.1016/j.tet.2015.02.067,10.1002/chem.201405558,10.1080/00397911.2014.965330,10.1055/s-0034-1378581,10.1139/cjc-2014-0217,10.1002/cjoc.201400174,10.1021/jo500821m,10.1021/ol5004737,10.1007/s10562-013-1136-x,10.1021/jo402386k,10.1002/adsc.201300452,10.7503/cjcu20130279,10.1002/adsc.201200771,10.1021/jo3018507,10.6023/cjoc1106222,10.1134/S1560090411030031,10.1039/c0ob01208d,10.1021/om100722f,10.1021/jo1015135,10.1021/jo101470r,10.1055/s-0030-1258528,10.1021/om100384q,10.1134/S1070427210050253,10.1021/ol1003252,10.1016/j.tet.2010.01.097,10.1021/jo901504n,10.1134/S0023158408040125,10.1134/S0965545X08030012,10.1002/ejoc.200700772,10.1021/ar600021z,10.1007/s11172-006-0556-9,10.1021/jo060299p,10.1055/s-2006-926379,10.1021/ja058621l,10.1021/ol0527936,10.1021/jo051660v,10.1021/ol0478133,10.1021/jo048721u,10.1021/jo048702k,10.1021/ol048517t,10.1021/ol048816i,10.1021/ol036027f,10.1002/chem.200204506,10.1021/ol034251z,10.1021/ol034283m,10.1016/S0040-4039(02)02666-7,10.1351/pac200375010063,10.2174/1385272023374111,10.1021/ol025731d,10.1021/jo010289i,10.1021/ol017300l,10.1039/b108808d,10.1016/S0010-8545(01)00401-5,10.1021/jo010609y,10.1021/ja0108640,10.1021/ol0069204,10.1002/1521-3773(20010401)40:7<1286::AID-ANIE1286>3.3.CO;2-9,10.1002/1521-3765(20001016)6:20<3706::AID-CHEM3706>3.3.CO;2-G,10.1021/ja993427i,10.1039/a907654i3/10/2022
330
109FALSEma951840e10.1021/ma951840ehttps://sci-hub.wf/10.1021/ma951840ehttps://doi.org/10.1021/ma951840eNiC-O ActivationGerryTRUE5321061996Percec, V
Nickel-catalyzed highly stereoselective ring opening of 7-oxa- and azanorbornenes with organic halides
MACROMOLECULES
Nickel-catalyzed ring-opening reactions of 7-heteroatom norbornadienes and norbornenes with various organic halides to give products with multiple stereocenters are described. Treatment of 7-oxabenzonorbornadiene (la) and 7-carbomethoxy-7-azabenzonorbornadiene (Ib) with aryl iodides (ArI) in the presence of NiCl2(PPh3)(2) and Zn powder gave the corresponding ring-opening addition products cis-1,2-dihydro-2-aryl-l-naphthol (2a-m) and methyl N-[cis-1,2-dihydro-2-aryl-l-naphthyl]-carbamate (3a-e) completely stereoselectively in 40-99% yields. The nickel system also catalyzes the reaction of highly substituted oxabicyclic [2.2.1] compounds (Ic-e) with organic halides (PhI, PhCH2Br, PhCHCHBr, and PhCBrCH2) to give the corresponding ring-opening products (4a-d, 5, 6a,b) that consist of four fixed stereocenters. Studies on the effect of solvent on the reaction of la with PhI show that CH3CN gives the highest yield of product 2a; no product 2a is observed when toluene, dichloromethane, methanol, DMF, or DMSO is used as solvent. Addition of extra PPh3 to the reaction mixture reduced the yield of 2a. A mechanism is proposed to account for the formation of these nickel-catalyzed ring-opening addition products.
CASE WESTERN RESERVE UNIV
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331
246FALSEol016526l10.1021/ol016526lhttps://sci-hub.wf/10.1021/ol016526lhttps://doi.org/10.1021/ol016526lNiC-O ActivationShihongTRUE27840282001Monteiro, AL
Regioregular and regioirregular poly(p-phenylene)s via Ni(O)-catalyzed homocoupling of arylene bismesylates
ORGANIC LETTERS
Head-to-head regioregular poly(p-phenylene)s (PPPs) were synthesized via Ni(O)-catalyzed polymerization of 2,2'-disubstituted 4,4'-bis[(methylsulfonyl)oxy]biphenyls (9). The corresponding regioirregular PPPs were prepared by the Ni(O)-catalyzed homopolymerization of 2-substituted 1,4-bis[(methylsulfonyl)oxy]benzenes (6) and by copolymerization of 6 with 9. The precursors of 6 and 9, i.e., 2-substituted 1,4-dihydroxybenzene (5) and 2,2'-disubstituted 4,4'-dihydroxybiphenyl (8), were synthesized by a synthetic method elaborated previously in our laboratory [J. Org. Chem. 1995, 60, 1066]. Head-to-head regioregular PPPs are crystalline and insoluble (except when the substituent is 4-tert-butylbenzoyl) while the corresponding regioirregular polymers are noncrystalline and soluble. The highest molecular weight regioirregular PPP was obtained by copolymerization of a 1:1 ratio of 6 with the corresponding 9. The influence of the size and the electronic properties of the substituent on the reactivity of monomers 6 and 9 and on the molecular weight of the regioirregular PPP is discussed. The highest molecular weight (M(n) = 34 790, corresponding to 176 phenylene groups relative to polystyrene standards) regioirregular PPP was obtained with a 4-fluorobenzoyl substituent. Fluorine both influences the reactivity of the leaving group and acts as more than one substituent since the hydrogen(s) ortho to it is (are) acidic.
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tlet.2008.07.060,10.1021/ja804672m,10.1021/jo8010254,10.2478/s11532-008-0017-4,10.1139/V08-038,10.1016/j.tet.2008.02.068,10.1021/ja710944j,10.1021/jo7022558,10.1016/j.tet.2007.10.091,10.1002/anie.200803193,10.1002/anie.200803814,10.1039/b803172j,10.1002/chem.200701418,10.1021/jo7019064,10.1016/j.tetlet.2007.08.089,10.1021/jo070912k,10.1021/jo0709448,10.1016/j.molcata.2007.03.060,10.1021/ja070321b,10.1021/om070094m,10.1055/s-2007-973875,10.1055/s-2007-965958,10.1016/j.tetlet.2007.01.175,10.1021/jo0623742,10.1007/s11172-007-0048-6,10.1002/chem.200600502,10.1002/chem.200601142,10.1002/ejoc.200600469,10.1021/jo061502j,10.1016/j.tetlet.2006.08.085,10.1016/j.tetlet.2006.07.085,10.1016/j.jcat.2006.06.020,10.1055/s-2006-942451,10.1055/s-2006-926424,10.1016/j.ccr.2006.01.001,10.1021/cc0600066,10.1002/ejoc.200600026,10.1016/j.tetlet.2006.01.145,10.1016/j.tetlet.2006.01.020,10.1039/b609064h,10.1021/jo0513764,10.1021/om050224w,10.1016/j.tetlet.2005.10.018,10.1021/jo051394l,10.1002/ejoc.200500279,10.1246/cl.2005.796,10.5059/yukigoseikyokaishi.63.312,10.1021/jo048300c,10.1021/om0492395,10.1021/ol047854z,10.1002/adsc.200404187,10.1016/j.tetlet.2004.09.020,10.1246/cl.2004.1322,10.1016/j.tetlet.2004.05.144,10.1016/j.molcata.2003.11.030,10.1016/j.tet.2004.03.072,10.1021/jo049940i,10.1081/SCC-120030306,10.1021/ja038752r,10.1021/op034104g,10.1021/om034187p,10.1021/ja038742q,10.1016/S0010-8545(03)00123-1,10.1021/jo034330o,10.1016/S1381-1169(03)00447-3,10.1021/ja036947t,10.1021/ol034948k,10.1002/adsc.200303036,10.1002/adsc.200303045,10.1002/marc.200350009,10.1021/ja035835z,10.1021/jo020640f,10.1016/S0040-4020(02)01351-0,10.1016/S0040-4020(02)01188-2,10.1021/ja027190t,10.1021/ja027716+,10.1016/S0040-4039(02)00863-8,10.1016/S0040-4039(02)00718-9,10.1016/S0040-4039(02)00716-5,10.1021/ol025673w Long 11/25/2021
332
209FALSEol050393c10.1021/ol050393chttps://sci-hub.wf/10.1021/ol050393chttps://doi.org/10.1021/ol050393cNiC-O ActivationLongTRUE1221982005Macklin, TK
NiCl2(PCy3)(2): A simple and efficient catalyst precursor for the Suzuki cross-coupling of aryl tosylates and arylboronic acids
ORGANIC LETTERS
[GRAPHICS] NiCl2(PCy3)(2) associated with PCy3 promotes the selective cross-coupling of aryltosylates with arylboronic acids under relatively mild reaction conditions, and a variety of functional groups are tolerated in both arenes. This is one of the simplest and most efficient experimental procedures for the coupling of arylboronic acids with aryl tosylates reported to date.
Queens Univ6/23/2005check table 4, and find the ligandCsp2_ar-Csp2_arE-NuOB
OSO2NEt2
B(OH)2ArylArylNa2CO3Ionic-CO3Weak0.33_xx10.1021/jo3001194,10.1021/ja907700e,10.1021/ol401727y,10.1021/ja200398c,10.1021/acscatal.9b00744,10.1021/ol9028308,10.1002/anie.201308391,10.1021/jo202037x,10.1039/c1sc00230a,10.1002/anie.201007325,10.1021/ol200267b,10.1021/ol301847m,10.1021/om500452c,10.1002/ejoc.201001519,10.1021/ja906477r,10.1039/c4qo00321g,10.1021/cs501045v,10.1021/jacs.7b04973,10.1021/ja210249h10.1002/ejoc.202100631,10.1055/a-1548-8362,10.1021/acs.orglett.1c00855,10.1016/j.tet.2021.131931,10.1055/a-1349-3543,10.1002/adsc.202001262,10.2533/chimia.2020.866,10.1002/cjoc.202000319,10.1021/acscatal.0c03334,10.1002/chem.202000289,10.1021/acs.jpcb.0c03844,10.1021/acs.orglett.0c01123,10.1021/acsomega.9b03989,10.1021/acs.orglett.9b04119,10.1021/acs.orglett.9b02621,10.1016/j.ccr.2019.03.006,10.1039/c9dt00455f,10.1002/adsc.201801586,10.1016/j.tetlet.2019.04.004,10.1021/acscatal.9b00744,10.1039/c8nj05288c,10.3390/catal9010076,10.1039/c8dt03882a,10.6023/cjoc201804027,10.1016/j.tet.2018.10.025,10.1021/acs.organomet.8b00589,10.1055/s-0037-1610273,10.1055/s-0037-1611053,10.1002/cctc.201800454,10.1039/c8nj00530c,10.1016/j.jorganchem.2018.01.019,10.1016/j.jelechem.2018.02.043,10.1002/ejoc.201701142,10.1002/ejoc.201701143,10.1055/s-0036-1590985,10.1039/c7gc02804k,10.1016/j.mcat.2017.06.033,10.1021/jacs.7b04973,10.1002/ejic.201700397,10.1126/sciadv.1700832,10.1021/acs.organomet.7b00109,10.1038/s41570-017-0025,10.1021/acs.joc.6b02666,10.1002/chem.201602683,10.1002/adsc.201600590,10.1021/acs.orglett.6b00547,10.1039/c6ra18997k,10.1039/c5dt04663g,10.1039/c6dt00252h,10.1002/chem.201502534,10.1002/ejoc.201500987,10.1002/ejoc.201500630,10.1002/adsc.201500304,10.1016/j.ica.2014.11.005,10.1021/cs5014927,10.1039/c4qo00321g,10.1039/c4ob01627k,10.1039/c5dt00435g,10.1021/jo502172c,10.1126/science.1259662,10.1021/om500452c,10.1021/ol5024344,10.1002/chem.201403141,10.1021/cs501045v,10.1021/ja5031744,10.1021/cr400230c,10.1002/anie.201308391,10.1021/jo402723e,10.1021/ja4118413,10.1039/c3ob41382a,10.1021/ol401727y,10.1055/s-0033-1338418,10.1021/ol401021x,10.1039/c3cs35521g,10.1002/ejoc.201200914,10.1038/NCHEM.1504,10.1021/op300236f,10.1039/c3ra44884c,10.1002/ejoc.201201061,10.1002/adsc.201200364,10.1021/ol301847m,10.1002/chem.201201394,10.1021/ol301681z,10.1002/ejoc.201200368,10.1021/ol300908g,10.1021/ol300671y,10.1021/jo3001194,10.1021/ol2031608,10.1021/ja210249h,10.1002/anie.201202136,10.1021/jo202037x,10.1246/bcsj.20110139,10.1246/cl.2011.907,10.1021/ja200398c,10.1021/ol200267b,10.1002/ejoc.201001519,10.1021/cr100259t,10.1002/anie.201007325,10.1039/c1sc00230a,10.1002/chem.201001943,10.1002/chem.201002273,10.1021/jo101718v,10.1021/jo100352b,10.1021/ol9028308,10.1021/ja906477r,10.1021/ja907700e,10.1021/ol7028096,10.1016/j.ccr.2007.03.011,10.1021/jo062385v,10.1021/jo0620359,10.1055/s-2007-967976,10.1002/anie.200603631,10.1021/ol051896lKelly12/30/2021
333
194FALSEol101592r10.1021/ol101592rhttps://sci-hub.wf/10.1021/ol101592rhttps://doi.org/10.1021/ol101592rNiC-O ActivationLongTRUE10520852010
Molander, GA
Directed ortho metalation methodology. The N,N-dialkyl aryl O-sulfamate as a new directed metalation as a group and cross-coupling partner for Grignard reagents
ORGANIC LETTERS
The ortho metalation (RLi/THF/-93 degrees C) of 3 followed by quench with a variety of electrophiles constitutes a new general route to substituted aryl O-sulfamates 4a-k. The Kumada-Corriu cross-coupling of O-sulfarnates 4e, 4n-s, and 6a with Grignard reagents gives biaryls 9a-m, and the use of 2-halo and boron derivatives 4h, 4i, and 4k for Suzuki-Miyaura cross-coupling and generation of benzynes leads to naphthols 7a and 7b. A relative metalation ranking of the OSONEt2 is reported.
Univ Penn9/17/2010Csp2_ar-Csp2_arE-NuOBOMsBF3KArylHetK3PO4Ionic-PO4Weak0.36TMx10.1039/c7cc06717h,10.1021/ja200398c,10.1039/c4qo00321g,10.1021/ol403209k,10.1002/chem.201003403,10.1021/jo2022982,10.1021/acs.orglett.6b01398,10.1002/anie.201101461,10.1021/acscatal.7b01058,10.1021/jo501291y,10.1021/acs.joc.6b01627,10.1016/j.tet.2012.04.005,10.1021/jo202037x,10.1021/ja2084509,10.1002/chem.201103784,10.1021/jo300547v,10.1246/cl.2011.913,10.1021/jo1024464,10.1021/jo3001194,10.1021/acscatal.9b0074410.1016/j.tet.2021.132431,10.1039/d1ob00955a,10.1039/d1ob01125a,10.1177/17475198211026479,10.1021/acs.joc.0c02151,10.1055/a-1349-3543,10.1080/14756366.2021.1900165,10.1021/acs.chemrev.0c00088,10.1002/cjoc.201900506,10.1021/jacs.9b08586,10.1021/acs.organomet.9b00543,10.1021/acscatal.9b00744,10.1002/ejoc.201801173,10.1007/3418_2018_19,10.1016/j.tet.2018.10.025,10.1002/adsc.201800729,10.1002/anie.201805486,10.1021/acs.orglett.7b03713,10.1021/acs.orglett.7b03669,10.1039/c7cc06717h,10.1021/acsomega.7b01165,10.1021/acscatal.7b01058,10.1002/adsc.201601105,10.1002/anie.201611720,10.1021/acscatal.7b00245,10.1021/acs.joc.6b01627,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1007/s41061-016-0043-1,10.1021/acs.orglett.6b01398,10.1021/acs.joc.6b00002,10.1016/bs.adomc.2016.07.001,10.1039/c6ob00628k,10.1002/anie.201504524,10.1002/ejoc.201500630,10.1016/j.tet.2015.02.088,10.1039/c4qo00321g,10.1039/c5ra12742d,10.1002/ejoc.201402919,10.1007/s11426-014-5138-3,10.1021/jo501291y,10.1021/jo500840s,10.1016/j.jct.2014.01.006,10.3762/bjoc.10.109,10.1016/j.inoche.2013.12.026,10.1021/cs4009946,10.1016/j.tetlet.2013.12.083,10.1021/ol403209k,10.1039/c4dt02374a,10.3184/174751914X13857348538466,10.6023/cjoc201307035,10.1039/c4dt00815d,10.1002/ejoc.201301372,10.1039/c3gc42182a,10.1039/c3ob41382a,10.1021/jo401867e,10.1021/ol401021x,10.1007/3418_2012_42,10.1039/c3sc22242j,10.1039/c3ob27128e,10.1039/c3sc00052d,10.1039/c3cs35521g,10.1021/op300236f,10.1002/adsc.201200364,10.1021/jo300547v,10.1002/ejoc.201200368,10.1016/j.tet.2012.04.005,10.1021/ol301221p,10.1021/ol3009842,10.1021/ol300671y,10.1021/ol300455e,10.1021/jo3001194,10.1021/om201271y,10.1002/chem.201103784,10.1021/jo2022982,10.1021/ja2084509,10.1039/c2ob26270c,10.1021/jo202037x,10.1021/ja207759e,10.1246/cl.2011.1254,10.1002/chem.201102644,10.1021/jo2015246,10.1021/jo201516v,10.1246/cl.2011.913,10.1246/cl.2011.907,10.1021/ol201469r,10.1002/adsc.201100101,10.1002/adsc.201000975,10.1021/ja200398c,10.1021/jo1024464,10.1021/ol200128y,10.1002/chem.201003403,10.1021/cr100259t,10.1002/anie.201101461,10.1002/chem.201002273Kelly12/2/2021
334
354FALSEchem.20110109110.1002/chem.201101091https://sci-hub.wf/10.1002/chem.201101091https://doi.org/10.1002/chem.201101091NiC-H ActivationGerryTRUE1627802011Itami, K
Nickel-Catalyzed C-H Arylation of Azoles with Haloarenes: Scope, Mechanism, and Applications to the Synthesis of Bioactive MoleculesCHEM-EUR J
Novel nickel-based catalytic systems for the C-H arylation of azoles with haloarenes and aryl triflates have been developed. We have established that Ni(OAc)(2)/bipy/LiOtBu serves as a general catalytic system for the coupling with aryl bromides and iodides as aryl electrophiles. For couplings with more challenging electrophiles, such as aryl chlorides and triflates, the Ni(OAc)(2)/dppf (dppf = 1,1'-bis(diphenylphosphino)ferrocene) system was found to be effective. Thiazoles, benzothiazoles, oxazoles, benzoxazoles, and benzimidazoles can be used as the heteroarene coupling partner. Upon further investigation, we discovered a new protocol for the present coupling using Mg(OtBu)(2) as a milder and less expensive alternative to LiOtBu. Attempts to reveal the mechanism of this nickel-catalyzed heterobiaryl coupling are also described. This newly developed methodology has been successfully applied to the syntheses of febuxostat (a xanthine oxidase inhibitor that is effective for the treatment of gout and hyperuricemia), tafamidis (effective for the treatment of TTR amyloid polyneuropathy), and texaline (a natural product having antitubercular activity).
Nagoya Univ8/1/2011yCsp2_ar-Csp2_arE-NuXHXHArylHetLiOtBuIonic-OtBu_xx10.1039/c5sc02942b,10.1021/ja210249h,10.1021/ja401344e,10.1021/ja306062c,10.1021/ja413131m,10.1021/acs.orglett.6b02265,10.1002/anie.20140382310.1002/pol.20210524,10.3762/bjoc.17.126,10.1080/00397911.2021.1949476,10.1039/d1cy00972a,10.1002/tcr.202100113,10.1039/d0sc06868c,10.1021/acs.orglett.1c00100,10.1016/j.mcat.2020.111294,10.1055/a-1335-7330,10.1002/slct.202002854,10.1021/acs.chemrev.9b00682,10.1039/d0cy00965b,10.1039/d0gc00917b,10.1016/j.chempr.2020.04.005,10.1002/slct.202001087,10.1007/s41061-020-0285-9,10.1002/slct.201903641,10.1002/ejoc.201901468,10.1002/adsc.201901078,10.1039/c9ob01883b,10.1021/acs.joc.9b02094,10.1016/j.tetlet.2019.151082,10.1002/aoc.4936,10.1021/acs.organomet.9b00060,10.1002/ajoc.201900069,10.1055/s-0037-1610676,10.1021/acs.chemrev.8b00507,10.1002/ejoc.201801610,10.3866/PKU.WHXB201810052,10.3390/catal9010076,10.1039/c8cs00036k,10.1021/acs.oprd.8b00164,10.1039/c8qo00227d,10.1002/adsc.201701506,10.1002/ajoc.201800002,10.1021/acs.joc.7b03055,10.1002/ajoc.201700446,10.1039/c7dt04560c,10.1039/c7ob02241g,10.1039/c8ra01478g,10.1039/c7ra13080e,10.1002/aoc.3855,10.1021/acs.joc.7b01711,10.1055/s-0036-1588487,10.6023/cjoc201703034,10.1002/ejoc.201700648,10.1039/c7qo00174f,10.1002/cssc.201700321,10.1039/c7nj00452d,10.1246/bcsj.20160365,10.1002/slct.201601747,10.3762/bjoc.12.272,10.1055/s-0036-1588303,10.1002/anie.201606529,10.1021/acs.orglett.6b02265,10.1021/acs.joc.6b00989,10.1007/s41061-016-0053-z,10.1002/jhet.2385,10.1002/asia.201600252,10.1021/acs.oprd.6b00106,10.1021/acs.joc.6b00113,10.1021/acs.organomet.6b00003,10.1016/j.jorganchem.2015.12.009,10.1039/c6ob00607h,10.1039/c5ob02496j,10.1039/c6gc02495e,10.1002/adsc.201500799,10.1080/00304948.2015.1088752,10.1002/anie.201507128,10.1021/acs.orglett.5b02458,10.1002/anie.201504735,10.1002/ejic.201500532,10.1016/j.tet.2015.03.066,10.1016/j.tet.2015.03.045,10.1016/j.tetlet.2015.03.004,10.1021/acs.joc.5b00019,10.1021/acs.orglett.5b00510,10.1021/ol503607h,10.1002/anie.201403729,10.1039/c5sc02942b,10.1016/j.cclet.2014.10.017,10.1055/s-0034-1379073,10.3987/COM-14-S(K)59,10.1039/c5ra08703a,10.1002/adsc.201400496,10.1039/c4dt01547a,10.1021/om500922n,10.1016/j.tetlet.2014.07.100,10.1016/j.tet.2014.07.022,10.1016/j.molcata.2014.03.017,10.1021/jo5013493,10.1002/chem.201403356,10.1016/j.tetlet.2014.05.019,10.1021/jo5010636,10.1002/anie.201403823,10.1021/ol500531m,10.7536/PC130904,10.1016/j.bmc.2014.02.017,10.1021/ol500542j,10.1021/ja413131m,10.1016/j.tetlet.2013.12.054,10.1002/anie.201307019,10.1039/c4qo00213j,10.1039/c4cc05307a,10.1039/c3ob42318b,10.1039/c3cy00503h,10.1039/c3sc52199k,10.1039/c3ra46955g,10.1016/j.tetlet.2013.10.071,10.1021/jo402106q,10.1021/ol4027073,10.1021/ja409803x,10.1002/ajoc.201300172,10.2174/15701786113109990034,10.1021/om400711d,10.1002/ejoc.201300704,10.1016/j.tet.2013.05.138,10.1021/sc4001109,10.1055/s-0033-1339193,10.1002/cctc.201200867,10.1002/asia.201300267,10.1016/j.tet.2012.10.048,10.5059/yukigoseikyokaishi.71.576,10.1021/ja401344e,10.1039/c3gc41027g,10.1039/c3np70006b,10.1039/c2cc37891d,10.1002/ejoc.201200914,10.3233/JAD-121729,10.1016/j.tetlet.2012.09.131,10.1021/ol302902e,10.1021/ol302635e,10.1055/s-0032-1317035,10.1016/j.tet.2012.05.091,10.1021/ja306062c,10.1016/j.tetlet.2012.05.155,10.1021/ol300937z,10.1016/j.tet.2012.03.001,10.1021/ol300570f,10.1007/s10593-012-0963-9,10.1021/ja210249h,10.1021/ol203235w,10.1007/3418_2012_32,10.1016/B978-0-12-396492-2.00031-X,10.1039/c2ob25425e,10.1351/PAC-CON-11-11-15,10.1002/anie.201106825,10.1002/anie.201201666,10.1039/c2sc20277h,10.1039/c2gc35457h,10.1021/ja209945x,10.1002/chem.201102644,10.1039/c1ob06387a12/29/2021
335
183FALSEol200267b10.1021/ol200267bhttps://sci-hub.wf/10.1021/ol200267bhttps://doi.org/10.1021/ol200267bNiC-O ActivationGerry8-FebTRUE961632011
Ackermann, L
Nickel-Catalyzed C-O Activation of Phenol Derivatives with Potassium Heteroaryltrifluoroborates
ORGANIC LETTERS
A general method based on nickel-catalyzed C-O activation of various phenol derivatives with potassium (hetero)aryltrifluoroborates has been developed. A large number of heterobiaryls can be easily obtained with yields up to 99% using methanesulfonate cross-coupling partners.
Univ Gottingen4/1/2011Csp2_ar-Nsp3E-NuOH
OSO2NMe2
HAryl
N(H)Aryl
NaOtBuIonic-OtBuWeak0.36_xx10.1039/c4qo00321g,10.1021/om500452c,10.1021/ol201437g,10.1021/jacs.7b04973,10.1021/om300566m,10.1021/acs.orglett.7b00556,10.1021/ja2084509,10.1021/ol301847m,10.1021/ol403209k,10.1021/ol401727y,10.1021/acscatal.8b01879,10.1021/cs501045v,10.1002/chem.201605095,10.1039/c1sc00230a,10.1021/acscatal.6b00865,10.1002/anie.20141087510.1002/aoc.6364,10.1055/a-1548-8362,10.1021/acs.joc.1c01057,10.1002/ejoc.202100194,10.1002/chem.202004437,10.1039/d0ra09639c,10.1021/acs.orglett.0c02909,10.1021/acs.chemrev.0c00088,10.1039/d0cy01159b,10.1016/j.mcat.2020.110915,10.1021/acs.orglett.9b02621,10.1021/acs.oprd.9b00194,10.1055/s-0037-1611732,10.1021/acs.joc.9b00703,10.1039/c8gc02611d,10.1002/adsc.201800504,10.1021/acscatal.8b01879,10.3390/molecules23071715,10.1016/j.jorganchem.2018.01.019,10.1002/aoc.4273,10.1021/acs.joc.7b02363,10.1021/acs.chemmater.7b02964,10.1021/jacs.7b04973,10.1039/c7ob01791j,10.1055/s-0036-1588806,10.1055/s-0036-1590819,10.1021/acs.orglett.7b01549,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1002/adsc.201601105,10.1016/j.tet.2017.01.050,10.1016/j.cclet.2016.11.002,10.1016/j.jorganchem.2016.12.029,10.1021/acs.organomet.6b00885,10.1071/CH17176,10.1002/chem.201605095,10.1002/slct.201601241,10.1016/j.tet.2016.08.058,10.1016/j.tet.2016.07.063,10.1002/tcr.201500305,10.1021/acscatal.6b00865,10.1021/acs.joc.6b00466,10.1021/acscatal.5b02021,10.1002/ejoc.201500987,10.1055/s-0034-1378871,10.1080/17415993.2015.1057512,10.1002/ejoc.201500226,10.1002/anie.201410875,10.1016/j.molcata.2014.10.031,10.1016/j.tetlet.2014.11.120,10.1039/c4qo00321g,10.1039/c5cy00802f,10.1039/c4cc08846h,10.1016/j.tetlet.2014.10.065,10.1021/om500452c,10.1021/jo501361k,10.1021/cs501045v,10.1002/anie.201404355,10.1002/adsc.201400201,10.1080/07328303.2014.907908,10.1021/om401028d,10.1021/ol403209k,10.1039/c4qo00233d,10.1039/c3ob42053a,10.1039/c4cc04939j,10.1039/c3ob41382a,10.1002/ejoc.201300592,10.1016/j.tetlet.2013.06.061,10.1021/ol401727y,10.1021/jo400539x,10.1055/s-0032-1316898,10.1021/ol4007162,10.1002/ejoc.201201263,10.1016/j.jfluchem.2012.12.001,10.1021/op300236f,10.1021/jo302112a,10.1016/j.tetlet.2012.08.015,10.1021/om300566m,10.1021/ol301847m,10.1016/j.tet.2012.05.054,10.1002/chem.201201394,10.1021/ol301681z,10.1021/ol300671y,10.1021/ol3002442,10.1021/ja300164d,10.1016/j.tet.2012.01.008,10.1021/ja2084509,10.1039/c2dt31271a,10.1002/anie.201202466,10.1021/ol201437g,10.1039/c1sc00230aKelly1/5/2022
336
129FALSEol201248c10.1021/ol201248chttps://sci-hub.wf/10.1021/ol201248chttps://doi.org/10.1021/ol201248cNiC-O ActivationGerryTRUE623272011Watson, MP
Palladium- and Nickel-Catalyzed Aminations of Aryl Imidazolylsulfonates and Sulfamates
ORGANIC LETTERS
A nickel complex derived from dppf, along with NaOt-Bu as the base, allowed for challenging aminations of aryl sulfamates. An improved functional group tolerance is observed in novel palladium-catalyzed aminations of imidazolylsulfonates with rac-BINAP as the ligand.
Univ Delaware7/1/2011Csp3-Csp2_arE-NuOHOMeHAlkylArylNo baseNo BaseStrong-0.28_10.1021/ja401344e,10.1021/ja413131m,10.1016/j.tet.2013.04.09610.1002/cjoc.202100508,10.1002/chem.202004375,10.1080/10406638.2021.1881130,10.1016/j.jscs.2020.101178,10.1021/acs.joc.0c02441,10.1002/adsc.201901142,10.1016/j.tetlet.2019.151105,10.1021/acs.orglett.9b02145,10.1021/acs.joc.8b03078,10.1039/c7dt03403b,10.1039/c7sc01750b,10.1021/acscatal.6b02477,10.1021/acs.orglett.6b02235,10.1055/s-0035-1562614,10.1002/adsc.201600654,10.1002/slct.201600411,10.1007/s11164-015-2273-1,10.1002/chem.201600865,10.1007/s10593-016-1856-0,10.3987/COM-15-13314,10.1055/s-0034-1381035,10.1016/j.tet.2015.07.060,10.1002/ps.3894,10.1016/j.tet.2015.03.066,10.1021/acs.organomet.5b00215,10.1002/ejoc.201403121,10.1021/jo502446k,10.1039/c5dt00032g,10.1021/jo501697n,10.1021/om500938u,10.1002/adsc.201400234,10.1002/chem.201403356,10.1021/ja503489b,10.1021/ol500701n,10.1021/cs401164z,10.1021/ja413131m,10.1021/ol402644y,10.1002/anie.201303994,10.1002/adsc.201300055,10.1016/j.tet.2013.04.096,10.1002/cmdc.201300114,10.1021/ja401344e,10.1016/j.tetlet.2012.12.091,10.1055/s-0032-1318331,10.1039/c3gc40162f,10.1016/j.tet.2012.08.095,10.1021/ja3079362,10.1002/chem.201202225,10.1002/ejoc.201200678,10.1021/ol300471a,10.1055/s-0031-1289680,10.1021/ol203043h,10.1039/c2ra20231j,10.1021/ol202271k,10.1021/ja206850s,10.1016/j.tetlet.2011.07.023Kelly1/19/2022
337
116FALSEol201437g10.1021/ol201437ghttps://sci-hub.wf/10.1021/ol201437ghttps://doi.org/10.1021/ol201437gNiC-O ActivationKellyTRUE567312011Yang, LM
Nickel(0)-Catalyzed Cyclization of N-Benzoylaminals for Isoindolinone Synthesis
ORGANIC LETTERS
A nickel(0) catalyst effectively mediates the cyclization of N-benzoyl aminals in the presence of a stoichiometric Lewis acid. This method enables preparation of a variety of isoindolinones with substitution on the benzoyl fragment and C-3 carbon. This reaction likely proceeds via an alpha-amidoalkylnickel(II) intermediate, which then may cyclize via either an electrophilic aromatic substitution or an insertion pathway.
Chinese Acad Sci7/15/2011Csp2_ar-Nsp3E-NuOH
OPO(OPh)2
HAryl
Morpholine
NaHIonic-HStrong0.04_xx10.1021/cs501045v,10.1002/adsc.201400460,10.1021/ol403209k,10.1021/jacs.7b04973,10.1002/anie.201410875,10.1021/acs.orglett.7b00556,10.1021/acscatal.8b0187910.1039/d0nj01610a,10.1016/j.mcat.2020.110915,10.1002/cjoc.201900506,10.1002/ejoc.202000117,10.1126/science.aaw3254,10.1055/s-0037-1611732,10.1021/acs.joc.9b00669,10.1021/acs.joc.9b00703,10.1039/c8nj05503c,10.1002/adsc.201800504,10.1021/acscatal.8b01879,10.1016/j.jorganchem.2018.01.019,10.1002/aoc.4273,10.1021/acs.orglett.8b00060,10.1021/jacs.7b04973,10.1039/c7ob01791j,10.1021/acs.orglett.7b01549,10.1039/c7dt01805c,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1016/j.tet.2017.01.050,10.1016/j.cclet.2016.11.002,10.1016/j.jorganchem.2016.12.029,10.1021/acscatal.6b02964,10.1002/tcr.201500305,10.1021/acs.joc.6b00466,10.1021/acscatal.5b02021,10.1039/c6dt02995g,10.1002/ejoc.201500226,10.1002/anie.201410875,10.1016/j.molcata.2014.10.031,10.1039/c4ob02586e,10.3987/COM-14-S(K)18,10.1002/adsc.201400460,10.1021/cs501045v,10.1002/anie.201404355,10.3762/bjoc.10.117,10.1021/om401028d,10.1016/j.bbrc.2014.02.067,10.1021/ja4118413,10.1021/ol403209k,10.1039/c3ob42053a,10.1039/c3ra46288a,10.1016/j.tet.2013.04.073,10.1002/adsc.201200389,10.2174/138527212800672646,10.1007/s11172-012-0130-6,10.1021/om300205c,10.1039/c2cc31718d,10.1039/c2ob25425e,10.1021/ol202058rchecked by Kelly12/15/2021
338
208FALSEol203322v10.1021/ol203322vhttps://sci-hub.wf/10.1021/ol203322vhttps://doi.org/10.1021/ol203322vNiC-O ActivationLongTRUE11915272012Watson, MP
Nickel-Catalyzed Amination of Aryl Phosphates through Cleaving Aryl C-O Bonds
ORGANIC LETTERS
The amination of triaryl phosphates was achieved using a Ni(II)-(sigma-Aryl) complex/NHC catalyst system In dioxane at 110 degrees C in the presence of NaH as base. Electron-neutral, -rich, and -deficient triaryl phosphates were coupled with a wider range of amine partners including cyclic and acyclic secondary amines, aliphatic primary amines, and anilines in good to excellent yields.
Univ Delaware3/2/2012TRUEFALSETRUECsp2_ar-Csp2E-NuOHOPivHArylVinylK3PO4Ionic-PO4Medium0.33_xxxLong added10.1039/c7cc06717h,10.1002/anie.201710241,10.1021/acscatal.6b00801,10.1021/acscatal.7b01058,10.1039/c3cc46663a,10.1021/acs.orglett.7b00556,10.1016/j.tet.2012.04.005,10.1002/anie.201308391,10.1002/anie.202011036,10.1021/jacs.7b04973,10.1039/d1cc00634g,10.1021/acscatal.7b00941,10.1021/ja307045r,10.1002/anie.201412051,10.1021/acscatal.9b0074410.1021/acscatal.1c05441,10.1021/jacs.1c05661,10.1002/chem.202101101,10.1021/acs.organomet.1c00085,10.1021/acs.joc.1c00592,10.1039/d1cc00634g,10.1039/d0sc06056a,10.1002/anie.202011036,10.1021/acs.organomet.0c00573,10.1002/adsc.202000820,10.1021/acs.chemrev.0c00088,10.1002/slct.202001578,10.1002/cctc.202000876,10.1021/acs.chemrev.9b00682,10.1021/acs.organomet.0c00338,10.1002/cjoc.201900506,10.1021/acs.orglett.0c00945,10.1021/acs.orglett.0c00983,10.1021/acsomega.9b04450,10.1002/anie.202001211,10.1002/adsc.201901398,10.1021/acscatal.9b02636,10.1021/acs.orglett.9b02577,10.1021/acs.orglett.9b02130,10.1039/c9ra02394a,10.1021/acs.orglett.9b00600,10.1021/acscatal.9b00744,10.1021/acs.organomet.8b00720,10.1007/3418_2018_19,10.1016/j.tet.2018.10.025,10.1039/c8cc07093h,10.1021/jacs.8b06966,10.1002/adsc.201800729,10.1002/anie.201805396,10.1039/c8ob01034j,10.1016/j.jorganchem.2018.01.019,10.1039/c7nj04701k,10.1002/aoc.4138,10.1021/acs.orglett.7b03713,10.1055/s-0036-1591853,10.1021/acs.orglett.7b03669,10.1021/acs.orglett.7b03560,10.1021/acs.joc.7b02588,10.1039/c7cc06717h,10.1002/anie.201710241,10.1002/aoc.3757,10.1002/anie.201706581,10.1002/anie.201707134,10.1021/jacs.7b04973,10.1002/anie.201706719,10.1021/acsomega.7b01165,10.1021/acs.orglett.7b01054,10.1021/acscatal.7b00941,10.1021/acscatal.7b01058,10.1021/acs.joc.6b02701,10.1021/acs.orglett.7b00556,10.1002/adsc.201601105,10.1002/anie.201611720,10.1021/acscatal.6b03344,10.1166/nnl.2017.2265,10.1021/acscatal.6b02964,10.1002/chem.201604061,10.1002/anie.201606955,10.1002/chem.201602150,10.1007/s41061-016-0043-1,10.1016/j.tetlet.2016.06.083,10.1021/acscatal.6b00801,10.1002/anie.201601899,10.1021/acs.joc.6b00289,10.1002/adsc.201500822,10.1021/acscatal.5b02058,10.1016/bs.adomc.2016.07.001,10.1039/c6cc08182g,10.1039/c5cc10005d,10.1039/c5sc03359d,10.1039/c5cy02235e,10.1039/c6ra07130a,10.1002/chem.201503414,10.1002/ejoc.201500734,10.1002/anie.201503204,10.1021/acs.orglett.5b01229,10.1021/acs.oprd.5b00123,10.1016/j.tet.2015.02.088,10.1021/acs.accounts.5b00051,10.1021/ja511236d,10.1016/j.tet.2015.02.011,10.1021/jacs.5b00538,10.1002/anie.201412051,10.1021/ja512498u,10.1071/CH15459,10.1039/c5sc00305a,10.1021/jo502260x,10.1021/ol5024344,10.1002/adsc.201400201,10.1038/nature13274,10.1002/aoc.3134,10.1002/anie.201308391,10.1021/ja4118413,10.1021/ja410883p,10.1039/c4ob01011f,10.1039/c4cs00206g,10.1016/j.tetlet.2013.08.018,10.1016/j.apcata.2013.04.009,10.1021/ja312087x,10.1021/ol303130j,10.1007/3418_2012_42,10.1039/c3cc46663a,10.1039/c2dt32008h,10.1021/ja307045r,10.1016/j.tet.2012.04.005Kelly11/9/2021
339
359FALSEjacs.7b0238910.1021/jacs.7b02389https://sci-hub.wf/10.1021/jacs.7b02389https://doi.org/10.1021/jacs.7b02389NiC-N ActivationLongTRUE4411272017Watson, MP
Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation
J AM CHEM SOC
We developed a strategy to harness alkyl amines as alkylating agents via C-N bond activation. This Suzuki Miyaura cross coupling of alkylpyridinium salts, readily formed from primary amines, is the first example of a metal-catalyzed cross coupling via C-N bond activation of an amine with an unactivated alkyl group. This reaction enjoys broad scope and functional group tolerance. Primary and secondary alkyl groups can be installed. Preliminary studies suggest a Ni-I/Ni-II catalytic cycle.
Univ Delaware4/19/2017TRUETRUEFALSEyCsp3-Csp2_arE-NuNB
Triphenylpyridinium+BF4-
B(OH)2AlkylArylKOtBuIonic-OtBuNi(I)/Ni(III)_xx10.1038/s41467-021-25222-1,10.1126/sciadv.aaw9516,10.1021/acs.orglett.8b01062,10.1021/acs.orglett.9b04497,10.1021/jacs.9b00111,10.1021/jacs.9b05224,10.1002/anie.202002271,10.1039/c9sc00783k,10.1021/acs.orglett.9b01016,10.1055/s-0037-1610084,10.1021/acs.orglett.9b0101410.1039/d2ta01146h,10.1021/acs.orglett.2c00317,10.1039/d2cc00369d,10.1055/s-0040-1719881,10.1039/d1cs01084k,10.1021/jacs.1c12350,10.1021/jacs.1c12622,10.1039/d1gc04184c,10.1021/acs.orglett.1c03870,10.1021/acs.joc.1c02499,10.1021/jacs.1c10150,10.1021/acs.orglett.1c03122,10.1038/s41467-021-27060-7,10.1002/anie.202112454,10.1039/d1qo01460a,10.1021/acs.orglett.1c03194,10.1021/jacs.1c09779,10.1002/adsc.202100940,10.3390/molecules26195947,10.1021/acs.orglett.1c02708,10.1039/d1cp02622d,10.1002/ajoc.202100438,10.1021/acs.joc.1c01555,10.1021/acs.orglett.1c02458,10.1021/acs.chemrev.1c00084,10.1038/s41467-021-25222-1,10.1016/j.chempr.2021.03.023,10.1039/d1cs00380a,10.1021/acs.orglett.1c01959,10.1021/jacs.1c05278,10.1021/acs.orglett.1c01758,10.1039/c9cs00571d,10.1021/acscatal.1c01860,10.1002/cctc.202100672,10.1021/acs.orglett.1c01716,10.1039/d1qo00660f,10.1039/d1qo00507c,10.1039/d1qo00798j,10.1039/d1sc01217g,10.1021/acscatal.1c01416,10.1016/j.tetlet.2021.153071,10.1039/d1qo00037c,10.1055/a-1479-6366,10.1039/d1sc00986a,10.1039/d1cc00039j,10.1039/d1sc01024g,10.1039/d0cs01107j,10.1007/s11426-020-9958-6,10.1002/ajoc.202100009,10.1039/d1ob00196e,10.1021/acs.orglett.1c00178,10.1002/anie.202016811,10.1021/acs.orglett.1c00346,10.1021/acs.orglett.0c04287,10.1021/acs.joc.0c02992,10.1007/s12039-020-01868-0,10.1039/d0cc07632e,10.1002/ejoc.202001193,10.1039/d0ob01807d,10.2174/1570179418666210224124931,10.1021/jacs.0c11172,10.1039/d0sc04585c,10.1021/acs.joc.0c01928,10.1039/d0cc05725h,10.7536/PC200607,10.1021/acscatal.0c03341,10.1002/anie.202010157,10.1021/jacs.0c08595,10.1038/s41467-020-18834-6,10.1039/d0sc03833d,10.1021/jacs.0c07492,10.1007/s11426-020-9838-x,10.1021/acs.joc.0c01509,10.3390/catal10091054,10.1039/d0cc04062b,10.1021/acs.joc.0c01274,10.1021/acs.orglett.0c01592,10.1002/anie.202006048,10.1002/adsc.202000457,10.1021/acs.oprd.0c00104,10.1002/anie.202002271,10.1021/jacs.0c04456,10.1021/jacs.0c03039,10.1039/d0cc01333a,10.1002/anie.201914555,10.1021/jacs.0c01724,10.1002/ajoc.202000163,10.1021/acs.orglett.0c00554,10.1002/anie.201911660,10.1021/acs.orglett.0c00736,10.1039/d0sc00225a,10.1002/chem.202000412,10.1002/ijch.201900166,10.1021/acs.orglett.9b04497,10.1021/jacs.9b12167,10.1021/jacs.9b12343,10.1055/s-0039-1690703,10.1039/c9cc08348k,10.1039/c9cc07072a,10.1039/c9ob02107h,10.1039/c9qo01175g,10.1021/acs.orglett.9b03899,10.1021/acs.orglett.9b03284,10.1021/jacs.9b07489,10.1039/c9sc03765a,10.1021/acscatal.9b03084,10.1039/c9cc05385a,10.1021/acs.orglett.9b02643,10.6023/A19040121,10.1002/adsc.201900576,10.1021/acs.orglett.9b02534,10.1021/acscatal.9b02440,10.1002/adsc.201900803,10.1002/adsc.201900551,10.1021/jacs.9b05224,10.1055/s-0037-1611878,10.1021/acs.orglett.9b02182,10.1021/acs.oprd.9b00194,10.1021/jacs.9b05671,10.1055/s-0037-1611852,10.1021/acs.chemrev.8b00628,10.1002/chem.201901397,10.1021/acs.orglett.9b01124,10.5059/yukigoseikyokaishi.77.614,10.1126/sciadv.aaw9516,10.1038/s41929-019-0292-9,10.1039/c9sc01083a,10.1021/jacs.9b02312,10.1021/acs.orglett.9b01097,10.1039/c9sc00783k,10.1021/jacs.9b02238,10.1021/acs.orglett.9b01014,10.1021/acs.orglett.9b01016,10.1002/anie.201814452,10.1002/chem.201900886,10.1021/acscatal.9b00218,10.1002/anie.201813689,10.1039/c8ob02786b,10.1021/jacs.9b00111,10.1021/acs.organomet.8b00720,10.1002/anie.201810261,10.1021/acscatal.8b04191,10.1039/c8qo01046c,10.1021/acscatal.8b03437,10.1002/chem.201804246,10.1002/anie.201809608,10.1039/c8cc07093h,10.1021/jacs.8b06458,10.1002/anie.201807640,10.1021/jacs.8b07103,10.6023/cjoc201803013,10.1002/anie.201806271,10.1055/s-0037-1610084,10.1021/acs.joc.8b00278,10.1021/acs.orglett.8b01062,10.1021/acscatal.8b00423,10.1039/c7cc09602j,10.1126/science.aar7335,10.1055/s-0036-1591523,10.1002/asia.201701694,10.1002/asia.201701655,10.1002/aoc.4107,10.1039/c7gc03141f,10.1021/acscatal.7b03432,10.1039/c7gc02775c,10.1002/ijch.201700044,10.1002/anie.201706896,10.1021/acs.orglett.7b01575,10.1021/acscatal.7b01405,10.1021/jacs.7b0527311/1/2021APR 192017FALSEFALSEFALSEFALSE139155313
340
279FALSEol300207810.1021/ol3002078https://sci-hub.wf/10.1021/ol3002078https://doi.org/10.1021/ol3002078NiC-O ActivationShihong17-MarTRUE419#N/A2012Shibasaki, M
Nickel(0)-Catalyzed Heck Cross-Coupling via Activation of Aryl C-OPiv Bonds
ORGANIC LETTERS
Using a Ni(dppf) catalyst generated in situ, Heck cross-coupling of aryl pivalates with a variety of olefin partners has been accomplished. This method represents one of the first examples of a C C cross-coupling via activation of a strong C-O bond with a nonorganometallic coupling partner. It enables the transformation of phenol-based substrates into styrenyl products without generation of a halogenated byproduct or the use of expensive triflate groups.
3/2/2012Csp2-Csp3E-NuOH
O(Ring-Opening)
H
Carbonyl
AlkylNo baseNo BaseWeak110.1021/ol502682q,10.1021/acs.orglett.9b01164,10.1002/anie.202002271,10.1021/acs.orglett.9b04497,10.1021/ja510653n,10.1039/c2cc33232a,10.1021/acscatal.0c00246,10.1039/c5cc03113c,10.1021/ol301119810.1039/d1nj04081b,10.1021/acs.cgd.1c00885,10.1002/tcr.202000108,10.1002/tcr.202000066,10.1002/cjoc.201900371,10.1016/j.tetlet.2019.151131,10.1248/cpb.c19-00215,10.1021/jacs.9b02220,10.3866/PKU.WHXB201807071,10.1039/c8dt02362j,10.1016/j.tet.2018.05.064,10.1039/c8cc05458d,10.1002/adsc.201800616,10.5059/yukigoseikyokaishi.76.781,10.1007/3418_2015_153,10.1002/chem.201703239,10.3987/REV-16-SR(S)5,10.1016/j.tetlet.2016.07.093,10.1021/acscatal.6b01227,10.1016/j.tetlet.2016.05.072,10.1016/j.tetlet.2015.10.097,10.1002/chem.201501568,10.1016/j.tet.2014.10.008,10.1016/j.poly.2014.07.018,10.1021/jo501882q,10.1021/ml500161v,10.1021/ol501397b,10.1039/c3sc52929k,10.3987/COM-13-S(S)60,10.1039/c3cc47587e,10.1021/ol402887z,10.1002/asia.201300251,10.6023/cjoc201301020,10.1016/j.saa.2013.03.082,10.1002/ejoc.201201635,10.1016/j.molstruc.2012.12.014,10.1016/j.poly.2013.01.010,10.1055/s-0032-1316846,10.1021/jo301803h3/24/2022
341
361FALSEol901684h10.1021/ol901684hhttps://sci-hub.wf/10.1021/ol901684hhttps://doi.org/10.1021/ol901684hNiC-H ActivationShihongFALSE16711#N/A2009Miura, M#N/ANickel-Catalyzed Direct Alkynylation of Azoles with Alkynyl BromidesORG LETT
The direct C-H alkynylation of azoles with alkynyl bromides proceeds efficiently in the presence of a nickel-based catalyst system. The reaction enables the introduction of various alkynyl groups bearing aryl, alkenyl, alkyl, and silyl substituents to the azole cores. In some cases, addition of a catalytic amount of CuI is observed to accelerate the direct coupling dramatically.
Osaka Univ9/17/2009_10.1002/cctc.201000223,10.1002/anie.200907040,10.1021/ja413131m,10.1021/ja401344e,10.1002/chem.201001631,10.1021/acscatal.6b01120,10.1039/c5cy01299f,10.1021/acs.joc.5b00669,10.1002/anie.200906996,10.1021/ol100699g,10.1002/chem.20110109110.1002/adsc.202100992,10.1002/adsc.202100823,10.1002/adsc.202100845,10.1016/j.tet.2021.132370,10.1039/d1ra05303e,10.1002/chem.202100475,10.1002/tcr.202100113,10.1021/acs.orglett.0c04243,10.2174/1385272825666210608115144,10.1002/chem.202002888,10.3390/molecules25112490,10.1016/j.chempr.2020.04.005,10.1002/anie.202002948,10.1021/acs.organomet.9b00060,10.1002/adsc.201801381,10.1039/c9cy00009g,10.1039/c8nj02964d,10.1021/acs.chemrev.8b00507,10.1039/c8qo01215f,10.2174/1385272823666191014154129,10.2174/1570179416666190329200616,10.1002/ijch.201800030,10.1039/c8cc03445a,10.1021/acs.organomet.8b00177,10.1002/ajoc.201800243,10.1021/acscatal.7b04395,10.1039/c7ob02438j,10.1039/c8ra03278e,10.1002/adsc.201700931,10.1039/c7nj03063k,10.1021/acs.joc.7b00775,10.1002/slct.201702265,10.1039/c7qo00327g,10.1021/acs.orglett.7b02247,10.1002/ejoc.201700788,10.1021/acs.orglett.7b01294,10.1002/anie.201611118,10.1002/anie.201610426,10.1002/chem.201605306,10.1021/acs.orglett.6b03287,10.1039/c7ra07105a,10.6023/cjoc201604044,10.1021/acscatal.6b02477,10.1021/jacs.6b08942,10.1007/s41061-016-0053-z,10.1021/acscatal.6b01120,10.1021/acs.orglett.6b01319,10.1021/acs.joc.6b00406,10.1021/acs.orglett.6b00821,10.1002/adsc.201500727,10.1039/c5cy01299f,10.1039/c6ob00179c,10.2174/1385272819666150423213643,10.1039/c6ob00106h,10.1021/acs.orglett.5b02678,10.1021/acscatal.5b01571,10.1002/chem.201501260,10.1021/jacs.5b07424,10.1016/j.tetlet.2015.08.001,10.1021/acs.joc.5b01093,10.1016/j.tet.2015.03.066,10.1021/acs.joc.5b00669,10.1002/chem.201501094,10.1055/s-0034-1380402,10.1246/cl.150024,10.1016/j.tet.2015.02.020,10.1002/adsc.201400857,10.6023/cjoc201412048,10.1002/chem.201405594,10.1039/c5dt02772a,10.1039/c5cc04390e,10.1039/c5cc03729h,10.1039/c5dt00032g,10.1039/c5cc01163a,10.1039/c4cc07574a,10.1016/j.tet.2014.10.068,10.1002/asia.201403052,10.1080/17415993.2014.934245,10.1016/j.tet.2014.07.022,10.1002/anie.201404579,10.1021/ol502030y,10.1016/j.cclet.2014.04.019,10.1021/cs500613t,10.1002/anie.201403782,10.1021/ja507704b,10.1021/ar5001499,10.1002/chem.201403356,10.1246/bcsj.20140099,10.1002/adsc.201400171,10.1021/ja501910e,10.1021/ol500542j,10.1002/anie.201309198,10.1002/ejoc.201301483,10.1016/j.bmcl.2014.01.034,10.1021/ja413131m,10.1039/c4ob01312c,10.1080/00397911.2013.771402,10.1002/ejoc.201301441,10.1002/ijch.201300044,10.6023/cjoc201211039,10.1021/ol401051d,10.1021/ja401344e,10.1039/c3ra41496e,10.1039/c3ra40669e,10.1039/c2cc37381e,10.1002/anie.201210013,10.1002/anie.201302210,10.1039/c3ob40448j,10.1055/s-0032-1316556,10.1002/adsc.201200374,10.1021/jo3013429,10.1016/j.catcom.2012.04.032,10.1002/chem.201200939,10.1021/jo3008385,10.1002/adsc.201200025,10.1002/chem.201200578,10.1021/ol300348w,10.1021/ol300514d,10.1002/cjoc.201100472,10.1002/chem.201200200,10.1021/ol203289v,10.1016/j.tet.2011.10.049,10.1021/ol203100u,10.1039/c2ce00029f,10.1002/anie.201106825,10.1002/anie.201107821,10.1039/c2cs35034c,10.1021/ol202383z,10.1016/j.tetlet.2011.07.092,10.1016/j.tetlet.2011.08.083,10.1021/ja206850s,10.1002/ejoc.201100659,10.1021/ja206002m,10.1055/s-0030-1260077,10.1002/chem.201101091,10.1021/ja111249p,10.5059/yukigoseikyokaishi.69.252,10.1021/ol1030298,10.1055/s-0030-1259332,10.1021/ja109732s,10.1071/CH11217,10.1039/c0cc02265a,10.1039/c1cs15082k,10.1002/ejoc.201000928,10.1002/cctc.201000223,10.1021/jo101433g,10.1021/jo101216m,10.1021/ol1016433,10.1021/ol1016756,10.1021/ol100699g,10.1021/ol100488v,10.1021/jo9025622,10.1021/ja910461e,10.1002/anie.200906755,10.1002/anie.200906996,10.1002/anie.200907040,10.1002/anie.201003179,10.1039/c0cc00778a,10.1039/c0cc02156c,10.1002/chem.200902916,10.1002/chem.201001631,10.1002/anie.200905419,10.1002/anie.200904776#N/A
342
139FALSEol300364s10.1021/ol300364shttps://sci-hub.wf/10.1021/ol300364shttps://doi.org/10.1021/ol300364sNiC-O ActivationGerryTRUE685452012Doyle, AG
Catalytic Enantioselective Desymmetrization of meso-Glutaric Anhydrides Using a Stable Ni-2-Schiff Base Catalyst
ORGANIC LETTERS
We describe the desymmetrization of meso-glutaric anhydrides to chiral hemiesters using a bench-stable homodinuclear Ni-2-(Schiff base) complex as the catalyst in good to excellent yield (up to 99%) and enantioselectivity (up to 94%). Using the opposite enantiomer of the catalyst, we obtained the same yield and enantioselectivity with the opposite configuration, thereby gaining access to both hemiester enantiomers.
Princeton Univ3/16/2012Csp3-Csp2_arE-NuOBOEtB(OH)2AllylArylNo baseNo BaseStrong-0.24_10.1021/jacs.7b04973,10.1021/acscatal.9b00744,10.1021/jo300547v,10.1038/NCHEM.2741,10.1039/c9cc08079a10.1039/d1qo01756j,10.1002/ejic.202100820,10.1055/a-1577-7638,10.1039/c9cs00571d,10.1021/acscatal.1c00536,10.1021/acs.organomet.1c00096,10.1021/acs.orglett.1c00488,10.1039/d0cy02059a,10.1039/d0ob00110d,10.1039/c9cc08079a,10.1038/s41929-019-0392-6,10.1039/c9sc03429c,10.1055/s-0039-1689973,10.1002/asia.201900641,10.1021/acs.orglett.9b01214,10.1002/anie.201900721,10.1021/acscatal.9b00744,10.1055/s-0037-1610682,10.1007/s11426-018-9359-4,10.1002/jhet.3375,10.1038/s41586-018-0628-7,10.1016/j.tet.2018.07.001,10.1039/c8ob00949j,10.1039/c7cy02362f,10.1002/adsc.201800179,10.1021/acscatal.8b00933,10.1016/j.jorganchem.2018.01.019,10.1021/jacs.7b12212,10.1039/c7gc03106h,10.1021/jacs.7b04973,10.1038/NCHEM.2741,10.1039/c7cc03037a,10.1055/s-0036-1588075,10.1016/j.tetlet.2016.11.076,10.1016/j.tetlet.2016.07.103,10.1021/acs.orglett.6b02058,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1002/chem.201601112,10.3987/COM-15-13402,10.1002/adsc.201501015,10.1016/j.crci.2015.11.016,10.1039/c6ra13584f,10.1039/c6ob01355d,10.1039/c5cc08386a,10.1002/adsc.201500058,10.1021/acs.orglett.5b00766,10.1021/acscatal.5b00026,10.1021/acs.orglett.5b00146,10.1002/chem.201406100,10.1002/anie.201410350,10.1002/ejoc.201403240,10.1002/chem.201404692,10.1021/ol503004a,10.1002/ejoc.201403043,10.1002/anie.201310193,10.1021/ja4111336,10.1039/c4ob01979b,10.1039/c4ra02941k,10.1039/c4sc00423j,10.1016/j.tet.2013.05.011,10.1002/anie.201303994,10.1016/j.tet.2012.12.062,10.1021/ja3079362,10.1021/jo301185h,10.1021/jo300547vKelly1/5/2022
343
181FALSEol300891k10.1021/ol300891khttps://sci-hub.wf/10.1021/ol300891khttps://doi.org/10.1021/ol300891kNiC-O ActivationKellyTRUE9717322012Jarvo, ER
Nickel-Catalyzed Cross-Coupling of Chromene Acetals and Boronic Acids
ORGANIC LETTERS
A modular and highly efficient protocol for the synthesis of 2-aryl- and heteroaryl-2H-chromenes is described. Under base-free conditions, readily accessible 2-ethoxy-2H-chromenes undergo C-sp3-O activation and C-sp3-C bond formation in the presence of an inexpensive nickel catalyst and boronic acids. This new strategy enables broad access to 2-substituted-2H-chromenes and has been applied to the late-stage incorporation of complex molecules, including the pharmaceuticals loratidine and indomethacin methyl ester.
Univ Calif Irvine8/17/2012Csp2_ar-Csp3E-NuOMg
OCCOMe
MgXArylAlkylNo baseNo BaseStrong-0.24_xx10.1021/ja4034999,10.1021/ol502583h,10.1002/anie.201503936,10.1021/ja307045r,10.1021/jacs.6b08075,10.1038/NCHEM.2741,10.1002/anie.201308666,10.1021/jacs.7b04973,10.1039/c7cc06106d,10.1021/jacs.1c03898,10.1021/jacs.9b00097,10.1021/ja5026485,10.1021/ol502682q,10.1021/ja311783k,10.1021/ja5076426,10.1021/ja3089422,10.1002/anie.20120252710.1021/acscatal.1c04235,10.6023/cjoc202106021,10.1021/acs.orglett.1c02458,10.1021/jacs.1c03898,10.1016/j.tetlet.2021.152947,10.1021/acs.orglett.0c04316,10.1055/s-0040-1706013,10.1021/acscatal.0c05484,10.2174/1570193X17999200723160453,10.1055/s-0040-1705987,10.1016/j.tet.2020.131201,10.1007/s11426-019-9732-5,10.1002/anie.201915454,10.1021/acs.joc.9b02705,10.1002/chem.202000215,10.1021/acs.orglett.9b03475,10.1021/acs.orglett.9b02910,10.1002/ajoc.201900409,10.1021/jacs.9b00097,10.1002/chem.201803642,10.1002/anie.201811343,10.3390/molecules24020294,10.1039/c8cc07093h,10.1002/anie.201806742,10.1021/acs.joc.8b00728,10.1016/j.jorganchem.2018.01.019,10.1002/cctc.201701601,10.6023/cjoc201709041,10.1021/acs.joc.8b00027,10.1021/acs.orglett.8b00169,10.1002/cjoc.201700664,10.1002/chem.201705463,10.1021/jacs.7b10855,10.1070/RCR4795,10.1055/s-0036-1590908,10.1021/jacs.7b04973,10.1039/c7cc06106d,10.1038/NCHEM.2741,10.1021/acscatal.6b02124,10.1021/jacs.6b08075,10.1002/adsc.201600590,10.1021/jacs.6b03384,10.1002/anie.201602075,10.1016/bs.adomc.2016.07.001,10.1039/c5qo00395d,10.1021/acs.joc.5b02557,10.1021/acs.orglett.5b03455,10.1021/acs.orglett.5b03072,10.1002/chem.201503647,10.1021/acs.orglett.5b02410,10.1021/acs.chemrev.5b00162,10.1016/j.tet.2015.04.066,10.1002/anie.201503936,10.1021/acs.accounts.5b00223,10.1021/acs.joc.5b00991,10.1021/ja510563d,10.1021/ja510980d,10.1016/S1872-2067(14)60217-5,10.1039/c4ra16452k,10.1021/ja5109084,10.1021/ol502583h,10.1021/ol502682q,10.1021/ja5076426,10.1021/ol5024344,10.1016/j.cclet.2014.04.019,10.1016/j.tet.2014.03.039,10.1021/jo5010636,10.1021/ja5039616,10.1021/ja5026485,10.1038/nature13274,10.1021/ja412159g,10.1002/anie.201308666,10.1021/ja410883p,10.1039/c4ob00744a,10.1039/c4cs00206g,10.1246/cl.130508,10.1021/ol4023358,10.1016/j.tet.2013.05.001,10.1021/ja4034999,10.1021/ol400625f,10.1021/ol400289v,10.1021/ja311783k,10.1021/ja312087x,10.1021/ol303465c,10.1021/ja3089422,10.1021/ol303130j,10.1002/anie.201302349,10.1002/anie.201208606,10.1002/anie.201207958,10.1021/ja3079362,10.1021/ja307045r,10.1002/anie.201202527Kelly1/11/2022
344
364FALSEol100699g10.1021/ol100699ghttps://sci-hub.wf/10.1021/ol100699ghttps://doi.org/10.1021/ol100699gNiC-H ActivationGerryTRUE1786#N/A2010Miura, M
Nickel- and Copper-Catalyzed Direct Alkynylation of Azoles and Polyfluoroarenes with Terminal Alkynes under O-2 or Atmospheric ConditionsORG LETT
The direct C-H alkynylation of azoles with terminal alkynes proceeds efficiently under a nickel/O-2 catalytic system. On the other hand, a copper/air catalyst enables the coupling of polyfluoroarenes with terminal alkynes. These catalyses provide new accesses to arylacetylenes through the formal direct Sonogashira coupling.
Osaka Univ5/21/2010yCsp2_ar-Csp1Nu-NuHHHHHetAlkyneLiOtBuIonic-OtBuNu-H_x10.1021/ja401344e,10.1021/ja413131m,10.1002/chem.201001631,10.1002/anie.201300459,10.1021/acscatal.6b01120,10.1002/cctc.20100022310.1016/j.jics.2021.100247,10.1002/adsc.202100992,10.1002/adsc.202100823,10.1002/adsc.202100741,10.1039/d1ra05303e,10.1039/d1gc01871j,10.1002/ejoc.202100618,10.1002/tcr.202100113,10.1039/d1ob00472g,10.1039/d1cc01233a,10.2174/1385272825666210608115144,10.1002/chem.202002888,10.3390/molecules25214970,10.1246/cl.200475,10.1002/cssc.202001165,10.3390/molecules25112490,10.1016/j.chempr.2020.04.005,10.1002/cctc.202000284,10.1002/ajoc.201900733,10.1039/c9ob02337b,10.1039/c9cc08735d,10.1021/acs.joc.9b01704,10.1039/c9sc02372k,10.5059/yukigoseikyokaishi.77.776,10.1016/j.tetlet.2019.06.003,10.1016/j.apcata.2019.04.020,10.1016/j.tetlet.2019.03.062,10.1021/acs.chemrev.8b00507,10.1039/c8qo01215f,10.1039/c8qo01105b,10.1021/acs.jpca.8b10306,10.1021/acs.chemrev.8b00022,10.1021/acs.organomet.8b00177,10.1002/ajoc.201800243,10.1002/ejoc.201800166,10.1021/acs.orglett.8b00772,10.1002/ejoc.201701586,10.1039/c7ob02438j,10.1039/c8ra03278e,10.1021/acs.joc.7b01489,10.1002/adsc.201700931,10.1002/anie.201708893,10.1039/c7ob01889d,10.1039/c7qo00327g,10.1021/acs.orglett.7b02247,10.1002/ejoc.201700788,10.1021/acs.orglett.7b01294,10.1002/chem.201605306,10.1039/c6ra26126d,10.1021/jacs.6b08942,10.1021/acs.orglett.6b02549,10.1007/s41061-016-0053-z,10.1021/acscatal.6b01120,10.1002/cctc.201600218,10.1038/ncomms11676,10.1021/acs.orglett.6b00289,10.1021/acs.orglett.6b00447,10.1002/adsc.201500727,10.1021/acscatal.5b02881,10.1016/bs.adomc.2016.08.001,10.1039/c6ob00179c,10.1039/c5ob02213d,10.2174/1385272819666150423213643,10.1007/3418_2015_116,10.1039/c6ob00106h,10.1039/c6qo00201c,10.1021/acs.orglett.5b02678,10.1021/acscatal.5b01571,10.1002/chem.201501260,10.1021/jacs.5b07424,10.1016/j.tetlet.2015.08.001,10.1002/anie.201504962,10.1021/acs.joc.5b01093,10.3184/174751915X14381883048110,10.1016/j.tetlet.2015.04.094,10.1002/anie.201412450,10.1016/j.tet.2015.02.020,10.1016/j.tetlet.2015.01.198,10.6023/cjoc201412048,10.1021/ol503238a,10.1002/chem.201405594,10.1039/c5sc02143j,10.1039/c5cc04390e,10.1039/c5cc03729h,10.1039/c5dt00032g,10.1039/c5cc02254a,10.1039/c4cc09330e,10.1016/j.tetlet.2014.11.033,10.1039/c5cc01412c,10.1039/c5gc00753d,10.1070/RCR4525,10.1002/asia.201403052,10.1021/om5008665,10.1002/adsc.201400198,10.1021/ol502030y,10.1021/cs500613t,10.1021/ja507704b,10.1002/chem.201403356,10.1246/bcsj.20140099,10.1021/ol501023n,10.1002/ejoc.201402091,10.1002/adsc.201400171,10.1021/ja501910e,10.1002/anie.201309198,10.1021/ja413131m,10.6023/cjoc201307024,10.1039/c4cy00544a,10.3987/COM-13-S(S)4,10.1039/c4ob01596g,10.1002/ejoc.201301441,10.1016/j.jfluchem.2013.05.023,10.1021/cr300527g,10.1021/ol401051d,10.1021/ja4026424,10.1016/j.tet.2012.10.048,10.1021/jo400162d,10.1021/ja401344e,10.1002/ejoc.201201689,10.1002/anie.201210013,10.1002/anie.201300459,10.1039/c2cc33706a,10.1039/c3ob40448j,10.1021/ol3028785,10.1055/s-0032-1316556,10.1002/adsc.201200683,10.1021/ja305801m,10.1016/j.tet.2012.04.003,10.1021/jo3008385,10.1021/ol300886k,10.1055/s-0031-1290965,10.1021/ol300514d,10.1021/ja301153k,10.1002/ejoc.201101676,10.1002/chem.201200200,10.1021/jo202644g,10.1021/ol203289v,10.1021/ja209992w,10.1021/ol203100u,10.1039/c2cc35927h,10.1002/anie.201204339,10.1002/anie.201106825,10.1002/anie.201203269,10.1039/c2cc30429e,10.1039/c2cc34659a,10.1039/c2cs15224j,10.1039/c2cs35034c,10.1016/j.tetlet.2011.08.083,10.1021/ja206850s,10.1246/cl.2011.1015,10.1002/ejoc.201100659,10.1021/ja206002m,10.1055/s-0030-1260077,10.1021/ol200855t,10.1002/chem.201100136,10.1021/ol200154s,10.1021/ja111249p,10.1021/cr100280d,10.1021/cr100379j,10.5059/yukigoseikyokaishi.69.252,10.1055/s-0030-1259332,10.1002/anie.201007733,10.1002/anie.201103945,10.1002/anie.201104735,10.1039/c0cs00125b,10.1039/c1cs15082k,10.1002/cctc.201000223,10.1021/jo101433g,10.1021/ja1045378,10.1002/anie.201003895,10.1002/chem.20100163112/29/2021
345
188FALSEol301119810.1021/ol3011198https://sci-hub.wf/10.1021/ol3011198https://doi.org/10.1021/ol3011198NiC-O ActivationGerryTRUE1049182012Ren, QH
Traceless Directing Group for Stereospecific Nickel-Catalyzed Alkyl-Alkyl Cross-Coupling Reactions
ORGANIC LETTERS
Stereospecific nickel-catalyzed cross-coupling reactions of benzylic 2-methoxyethyl ethers are reported for the preparation of enantioenriched 1,1-diarylethanes. The 2-methoxyethyl ether serves as a traceless directing group that accelerates cross-coupling. Chelation of magnesium ions is proposed to activate the benzylic C-O bond for oxidative addition.
Shanghai Univ6/15/2012Csp2-Csp3E-EOXOHX
Carbonyl
AlkylNo baseNo BaseStrong-0.81_10.1021/ol3013342,10.1021/ja5029793,10.1021/acscatal.9b00521,10.1021/acscatal.0c00246,10.1039/c3ob40232k,10.1039/c5cc03113c,10.1021/ja510653n,10.1021/ol502682q,10.1021/acs.orglett.9b0116410.1002/anie.202114731,10.1021/acscatal.1c04143,10.1039/d1qo01219c,10.1016/j.jorganchem.2021.122042,10.1002/anie.202014660,10.1021/acs.orglett.0c03342,10.7536/PC200607,10.1039/d0ob01083a,10.1002/adsc.202000799,10.1021/acscatal.0c01842,10.1002/ejoc.202000575,10.1021/acs.orglett.0c00554,10.1021/acscatal.0c00246,10.1002/ajoc.202000004,10.1039/c9dt02819f,10.1002/chem.201903668,10.1021/acs.orglett.9b02788,10.1002/ijch.201900072,10.1016/j.tet.2019.06.034,10.1021/acs.orglett.9b01164,10.1002/ejoc.201900098,10.1021/acs.joc.9b00633,10.1021/acs.orglett.9b00692,10.1021/acscatal.9b00521,10.1002/chem.201803642,10.1021/acs.organomet.8b00720,10.1039/c8qo01044g,10.1021/acs.orglett.8b03539,10.1021/acscatal.8b03930,10.1021/jacs.8b09191,10.1021/acs.orglett.8b02771,10.1021/acscatal.8b02784,10.1038/s41467-018-06019-1,10.1038/s41467-018-04646-2,10.1021/acs.orglett.7b03514,10.1016/bs.aihch.2017.10.001,10.1002/cjoc.201700071,10.1002/anie.201705520,10.1021/acs.orglett.7b01588,10.6023/cjoc201703042,10.1002/anie.201702857,10.1021/acs.orglett.7b01128,10.1021/jacs.7b01705,10.1055/s-0036-1588132,10.6023/cjoc201610009,10.1021/acs.orglett.6b03158,10.1039/c6ob01668e,10.1021/acs.cgd.6b00494,10.1055/s-0035-1562442,10.1007/s41061-016-0042-2,10.6023/cjoc201602007,10.1021/acs.orglett.6b01134,10.1021/jacs.6b01533,10.1002/anie.201600697,10.7536/PC150906,10.1002/cctc.201500724,10.1021/jacs.5b06255,10.1021/jacs.5b06466,10.1002/adsc.201400970,10.1039/c5ra18890c,10.1039/c5cc03113c,10.1039/c5qo00224a,10.1021/ja509077a,10.1021/ja510653n,10.1016/j.tet.2014.10.061,10.1002/chem.201405296,10.1021/ol502682q,10.1016/j.jorganchem.2014.08.015,10.1021/om5004682,10.1021/ja508067c,10.1021/ja05064586,10.1055/s-0033-1339126,10.1002/chem.201402509,10.1021/jo500507s,10.1002/chem.201402302,10.1021/ja5029793,10.1016/j.tet.2013.11.104,10.1016/j.jorganchem.2013.12.047,10.1055/s-0033-1340151,10.1039/c4cc04962d,10.1055/s-0033-1340061,10.1021/ja407589e,10.1055/s-0033-1339435,10.1055/s-0033-1339297,10.1016/j.tetlet.2013.06.009,10.1021/ja4030462,10.1021/ja402922w,10.1055/s-0032-1318237,10.1021/ja311045f,10.1039/c3sc51098k,10.1039/c3ob40232k,10.1021/ol3028913,10.1021/ol3013342Kelly1/20/2022
346
220FALSEol301334210.1021/ol3013342https://sci-hub.wf/10.1021/ol3013342https://doi.org/10.1021/ol3013342NiC-O ActivationGerryTRUE1491712012Gong, HG
Ketone Formation via Mild Nickel-Catalyzed Reductive Coupling of Alkyl Halides with Aryl Acid Chlorides
ORGANIC LETTERS
The present work highlights unprecedented Ni-catalyzed reductive coupling of unactivated alkyl iodides with aryl acid chlorides to efficiently generate alkyl aryl ketones under mild conditions.
Shanghai Univ7/6/2012Csp3-Csp2_arE-EOXOAcBrAllylArylNo baseNo BaseMedium0.31_10.1002/chem.201601320,10.1039/c9sc03347e,10.1039/c5cc03113c,10.1021/ja5029793,10.1039/c7cc06106d,10.1021/acscatal.9b00521,10.1021/jacs.0c12462,10.1039/c7sc03140h,10.1021/acs.orglett.7b00831,10.1039/c3ob40232k,10.1021/ol502682q,10.1021/jacs.0c13093,10.1021/jo302086g,10.1021/acs.orglett.9b01014,10.1021/acs.joc.5b00135,10.1021/jacs.9b05224,10.1039/c7cc01932g10.1002/anie.202200215,10.1021/acs.orglett.2c00207,10.1002/chem.202103643,10.1021/acscatal.1c04239,10.1039/d1qo01474a,10.1021/acs.joc.1c01625,10.1021/jacs.1c06271,10.1039/d1nj02677a,10.1021/jacs.1c05567,10.1021/acs.joc.1c01073,10.1021/acs.orglett.1c01649,10.1021/jacs.1c03459,10.1039/d1nj01732b,10.1021/acscatal.1c01416,10.1039/d1sc01731d,10.1126/science.abh2623,10.1021/acs.orglett.1c00812,10.1021/acsmedchemlett.0c00673,10.1021/jacs.0c13093,10.1021/jacs.0c12462,10.1055/s-0040-1707342,10.1002/anie.202010737,10.1021/acsomega.0c04181,10.1002/ijch.202000069,10.1021/acscatal.0c01842,10.1021/acscatal.0c02454,10.1021/acs.joc.0c00549,10.1021/acs.oprd.0c00134,10.1021/jacs.0c01475,10.1080/16583655.2020.1843872,10.1002/anie.201912753,10.1039/c9sc03347e,10.1002/asia.201900904,10.1016/j.tet.2019.06.034,10.1021/jacs.9b05224,10.1021/acs.oprd.9b00232,10.1021/acs.orglett.9b01987,10.1039/c9cc03737c,10.1002/ajoc.201900163,10.1039/c9qo00066f,10.1021/acs.orglett.9b01014,10.1021/acscatal.9b00521,10.6023/cjoc201806038,10.1021/jacs.8b13534,10.1016/j.molstruc.2018.08.043,10.1021/jacs.8b12025,10.1021/acs.orglett.8b02498,10.1021/acs.orglett.8b02771,10.1002/anie.201805118,10.1002/anie.201803228,10.1021/acs.orglett.8b01327,10.3390/molecules23061449,10.1021/acs.orglett.8b00235,10.1021/acs.orglett.8b00114,10.1039/c7sc03140h,10.1016/bs.aihch.2017.10.001,10.1021/jacs.7b08064,10.1039/c7cc06106d,10.1002/cjoc.201700071,10.1055/s-0036-1588793,10.1055/s-0036-1588464,10.1021/acs.orglett.7b01598,10.1021/acs.joc.7b01334,10.1039/c7cc01932g,10.1002/anie.201703400,10.1021/acs.orglett.7b01208,10.1021/acs.orglett.7b00831,10.1055/s-0036-1588132,10.1039/c7sc00243b,10.1021/acs.joc.6b02830,10.1002/chem.201603832,10.1002/anie.201607959,10.1038/NCHEM.2587,10.1021/acs.orglett.6b02665,10.1021/acs.cgd.6b00494,10.1055/s-0035-1562442,10.1021/acs.orglett.6b01837,10.1007/s41061-016-0042-2,10.1021/jacs.6b04818,10.1021/acs.orglett.6b01134,10.1002/chem.201601320,10.1021/jacs.6b01533,10.1021/jacs.6b00250,10.1002/ejoc.201501349,10.1039/c6ob02269c,10.1055/s-0035-1560531,10.1021/acs.orglett.5b02716,10.1021/jacs.5b06255,10.1002/chem.201501543,10.1021/jacs.5b06466,10.1002/adsc.201500346,10.1002/ejoc.201500784,10.1021/jacs.5b04892,10.5059/yukigoseikyokaishi.73.649,10.1021/acs.accounts.5b00057,10.1002/adsc.201400970,10.1021/acs.joc.5b00135,10.1039/c4cc08703h,10.1039/c5cc03113c,10.1039/c5qo00224a,10.1021/ja509077a,10.1016/j.tet.2014.10.061,10.1021/ol503043r,10.1002/tcr.201402058,10.1002/chem.201405223,10.1002/chem.201405296,10.1021/ol502682q,10.1016/j.jorganchem.2014.08.015,10.1021/om5004682,10.1021/ja508067c,10.1021/ol501495d,10.1055/s-0033-1339126,10.1002/chem.201403093,10.1002/chem.201402509,10.1021/jo500905m,10.1021/jo500507s,10.1002/chem.201402302,10.1021/ja5029793,10.1016/j.jorganchem.2013.12.047,10.1515/pac-2014-5032,10.1055/s-0033-1340151,10.1021/jo402526z,10.1080/00397911.2014.924141,10.1039/c3cc47633b,10.1039/c3ra47813k,10.1039/c3cc47780k,10.1055/s-0033-1338520,10.1016/j.tet.2013.08.067,10.1021/jo401936v,10.1021/ja407589e,10.1055/s-0033-1339435,10.1007/s11426-013-4880-2,10.1021/jo400803s,10.1021/ja4030462,10.1021/ja402922w,10.1021/ic302590g,10.1021/ol303366u,10.1021/ja309176h,10.1039/c3ob40232k,10.1021/jo302086gKelly1/20/2022
347
367FALSEol900159a10.1021/ol900159ahttps://sci-hub.wf/10.1021/ol900159ahttps://doi.org/10.1021/ol900159aNiC-H ActivationShihongTRUE18312#N/A2009Miura, M
Nickel-Catalyzed Direct Arylation of Azoles with Aryl BromidesORG LETT
Nickel catalyst systems for the direct C2 arylation of oxazoles and thiazoles have been developed. The catalyst systems are cost-efficient and allow the use of various aryl bromides in the C-H arylation of azoles.
Osaka Univ4/16/2009Csp2_ar-Csp2_arNu-NuMgHMgXHArylHetLiOtBuIonic-OtBuNu-M_10.1021/ja210249h,10.1021/ja401344e,10.1021/ja413131m,10.1002/chem.201001631,10.1016/j.tet.2013.04.096,10.1021/ol901684h,10.1021/ol900778m,10.1002/chem.201101091,10.1002/cctc.201000223,10.1002/anie.200906996,10.1039/c5sc02942b,10.1021/ja306062c10.3390/molecules26144385,10.1002/chem.202100475,10.1002/tcr.202100113,10.1055/a-1430-5100,10.1021/acs.orglett.1c00100,10.1039/d0ob02510k,10.1039/d0ob02134b,10.1055/a-1335-7330,10.7536/PC200607,10.1080/10406638.2018.1517808,10.1021/acs.chemrev.9b00682,10.1002/aoc.5869,10.1039/d0gc00917b,10.1021/acs.orglett.0c00994,10.1016/j.chempr.2020.04.005,10.1039/d0ra01845g,10.1021/acs.joc.9b02122,10.1002/slct.201903641,10.1039/c9ob01883b,10.1021/acs.joc.9b02094,10.1002/adsc.201900641,10.1016/j.tetlet.2019.06.026,10.1021/acs.organomet.9b00060,10.1007/s11426-018-9409-3,10.1039/c9cy00009g,10.1055/s-0037-1610676,10.1021/acs.chemrev.8b00507,10.6023/cjoc201807050,10.3390/catal9010076,10.1021/acs.accounts.8b00408,10.1002/ejoc.201800533,10.1002/adsc.201800728,10.1021/acs.oprd.8b00164,10.1016/j.progpolymsci.2018.06.002,10.1021/acs.orglett.8b01618,10.1055/s-0037-1609718,10.1039/c8qo00227d,10.1002/adsc.201701506,10.1021/acs.orglett.8b00530,10.1002/ajoc.201700446,10.1039/c7dt04560c,10.1039/c7qo00318h,10.1021/acs.orglett.7b01938,10.6023/cjoc201703034,10.1002/chem.201605657,10.1002/cssc.201700321,10.1039/c7nj00452d,10.1055/s-0036-1588936,10.1246/bcsj.20160365,10.1002/slct.201601747,10.1021/acscatal.6b02477,10.1002/cjoc.201600442,10.1007/s41061-016-0053-z,10.1021/acscatal.6b00678,10.1002/asia.201600252,10.1021/acs.organomet.6b00003,10.1021/acs.chemrev.5b00482,10.1002/adsc.201500993,10.1039/c6ra18997k,10.1002/anie.201507128,10.1021/acs.organomet.5b00733,10.1021/acs.orglett.5b02458,10.1016/j.jorganchem.2015.03.023,10.1002/anie.201504735,10.1016/j.tet.2015.03.066,10.1246/cl.150024,10.1021/acs.joc.5b00019,10.1021/acs.orglett.5b00510,10.1002/aoc.3263,10.1021/ol503556x,10.1039/c5sc02942b,10.1039/c5dt00032g,10.1039/c4ob02586e,10.1016/j.cclet.2014.10.017,10.1039/c4ra15384g,10.1055/s-0034-1379073,10.1039/c4dt01547a,10.1021/ol502314p,10.1016/j.tet.2014.07.022,10.1016/j.tet.2014.04.065,10.1002/chem.201403356,10.1246/bcsj.20140099,10.1021/jo5010636,10.1016/j.jorganchem.2013.12.055,10.1021/ol500531m,10.1246/bcsj.20130166,10.1021/ja413131m,10.1002/asia.201301371,10.1039/c4ra09092f,10.1039/c4cc05307a,10.3987/COM-13-S(S)13,10.1039/c4ra00559g,10.1080/00397911.2013.771402,10.1021/ja409803x,10.1021/om400711d,10.1016/j.tet.2013.04.096,10.1016/j.tet.2013.04.031,10.1021/jo400692p,10.5059/yukigoseikyokaishi.71.576,10.1002/jccs.201200413,10.1021/ja401344e,10.1055/s-0032-1318237,10.1021/ol303567t,10.1007/s11164-012-0578-x,10.1039/c3cc43915a,10.1002/ejoc.201200914,10.1055/s-0032-1317035,10.1016/j.tet.2012.05.091,10.1002/cctc.201200155,10.1021/ja306062c,10.1021/ol301517y,10.1021/ol300232a,10.1002/ejoc.201200050,10.1055/s-0031-1289692,10.2174/157019312799079884,10.1021/ja210249h,10.1039/c2cc34238c,10.1039/c2ra20366a,10.1002/anie.201106825,10.1021/om200819c,10.3762/bjoc.7.187,10.1021/ol201779n,10.1021/ol2021109,10.1021/ja206850s,10.1002/tcr.201100023,10.1021/ja2047717,10.2174/138527211796367291,10.1055/s-0030-1260077,10.1002/chem.201101091,10.1002/ejoc.201100238,10.1021/jo200452x,10.1002/chem.201100136,10.1016/j.molcata.2011.03.007,10.1002/adsc.201000723,10.1055/s-0030-1259727,10.1021/ja111249p,10.1002/chem.201002290,10.1021/cr100198w,10.5059/yukigoseikyokaishi.69.252,10.1021/jo102175f,10.1055/s-0030-1259332,10.1002/chem.201002354,10.1002/chem.201002787,10.1039/c1ob05223c,10.1002/ejoc.201000928,10.1021/ja103050x,10.1002/cctc.201000223,10.5059/yukigoseikyokaishi.68.1132,10.1021/jo101433g,10.1021/ja105368p,10.1055/s-0030-1258046,10.1021/ol101777x,10.1021/ol100488v,10.1021/ja100354j,10.1021/ja910900p,10.1021/jo100148x,10.1021/jo9025622,10.1002/cctc.200900294,10.1016/j.ccr.2009.07.023,10.1021/jo902515z,10.1021/ol9028034,10.1002/anie.200906996,10.1002/anie.201004097,10.1039/c0cc00778a,10.1002/chem.201001631,10.1039/c0dt00104j,10.1039/b919396k,10.1021/op900221v,10.1080/00397910903353739,10.1016/j.tet.2009.10.015,10.1055/s-0029-1217131,10.1016/j.tet.2009.09.011,10.1055/s-0029-1216977,10.1055/s-0029-1216987,10.1021/jo901316b,10.1021/ol901684h,10.1021/ol9011212,10.1021/ol900778m,10.1002/anie.20090477612/28/2021
348
192FALSEol301847m10.1021/ol301847mhttps://sci-hub.wf/10.1021/ol301847mhttps://doi.org/10.1021/ol301847mNiC-O ActivationShihongTRUE10517542012Garg, NK
Nickel-Catalyzed Reductive Coupling of Aryl Halides with Secondary Alkyl Bromides and Allylic Acetate
ORGANIC LETTERS
A room-temperature Ni-catalyzed reductive method for the coupling of aryl bromides with secondary alkyl bromides has been developed, providing C(sp(2))-C(sp(3)) products in good to excellent yields. Slight modification of this protocol allows efficient coupling of activated aryl chlorides with cyclohexyl bromide and aryl bromides with allylic acetate.
Univ Calif Los Angeles
8/17/2012Csp2_ar-Nsp3E-NuOH
OCONEt2
HAryl
Morpholine
NaOtBuIonic-OtBuMedium0.31_10.1021/ol401727y,10.1021/acs.joc.6b01627,10.1021/jacs.7b04973,10.1021/acscatal.6b00801,10.1021/ol403209k,10.1021/om500452c,10.1002/chem.201605095,10.1021/acscatal.8b01879,10.1002/adsc.201400460,10.1021/acscatal.1c04800,10.1002/anie.201410875,10.1021/acs.orglett.7b00556,10.1021/cs501045v,10.1021/acscatal.8b03436,10.1039/c4qo00321g,10.1021/acscatal.6b00865,10.1021/acscatal.7b0094110.1002/hlca.202100184,10.1021/acscatal.1c04800,10.1002/ejoc.202100194,10.1002/ajoc.202100043,10.1002/adsc.202000794,10.1021/acscatal.0c03334,10.1021/acs.chemrev.0c00088,10.1002/cctc.202000876,10.1021/acs.orglett.0c02320,10.1039/d0nj01610a,10.1039/d0nj01139h,10.1021/acs.orglett.0c01937,10.1021/acs.orglett.0c01600,10.1007/s41061-020-0300-1,10.1021/acs.orglett.9b02858,10.1055/s-0037-1611732,10.1021/acs.joc.9b00703,10.1002/ejoc.201900109,10.1021/acs.jpcc.8b08357,10.1007/3418_2018_19,10.1021/acscatal.8b03436,10.1021/jacs.8b08190,10.1002/adsc.201800729,10.1021/acs.orglett.8b01758,10.1021/acscatal.8b01879,10.3390/molecules23071715,10.1016/j.jorganchem.2018.01.019,10.1002/aoc.4273,10.1021/acs.orglett.8b00060,10.1055/s-0036-1591853,10.1021/acs.chemrev.7b00588,10.1021/acscatal.7b03215,10.1021/jacs.7b04973,10.1039/c7ob01791j,10.1055/s-0036-1590819,10.1021/acs.orglett.7b01549,10.1021/acscatal.7b00941,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1016/j.jorganchem.2016.12.029,10.1021/acscatal.6b03277,10.1002/chem.201605095,10.1021/acs.joc.6b01627,10.1002/anie.201606979,10.1002/anie.201606955,10.1002/chem.201601584,10.1002/tcr.201500305,10.1007/s41061-016-0043-1,10.1021/acscatal.6b00801,10.1021/acscatal.6b00865,10.1021/acs.joc.6b00289,10.1021/acscatal.5b02021,10.1016/bs.adomc.2016.07.001,10.1039/c6ob01307d,10.1039/c6ra14367a,10.1021/acs.oprd.5b00314,10.1002/ejoc.201500987,10.1002/ejoc.201500734,10.1002/ejoc.201500630,10.1002/adsc.201400850,10.1016/j.tetlet.2015.04.069,10.1021/acs.orglett.5b00766,10.1002/ejoc.201500226,10.1002/anie.201500404,10.1002/anie.201410875,10.1021/ed500158p,10.1016/j.ica.2015.01.005,10.1021/ja512498u,10.1016/j.molcata.2014.10.031,10.1039/c4qo00321g,10.1039/c4cc06445c,10.1021/ja5099935,10.1016/j.ica.2014.08.012,10.1021/om500452c,10.1002/adsc.201400460,10.1021/ol5024344,10.1021/cs501045v,10.1002/anie.201404355,10.1002/adsc.201400201,10.1038/nature13274,10.1021/ja412107b,10.1021/jo402723e,10.1021/ja4118413,10.1021/ja411911s,10.1021/ja410883p,10.1021/ol403209k,10.1039/c4qo00233d,10.1039/c3ob42053a,10.1039/c3ob41382a,10.1595/147106713X672311,10.1021/ol401727y,10.1021/ol401449b,10.1002/chem.201300229,10.1021/ol303130j,10.1039/c3cs60228a,10.1021/op300236fKelly11/25/2021
349
369FALSEncomms1155410.1038/ncomms11554https://sci-hub.wf/10.1038/ncomms11554https://doi.org/10.1038/ncomms11554NiC-N ActivationLongTRUE20612542016Garg, NK
A two-step approach to achieve secondary amide transamidation enabled by nickel catalysisNAT COMMUN
A long-standing challenge in synthetic chemistry is the development of the transamidation reaction. This process, which involves the conversion of one amide to another, is typically plagued by unfavourable kinetic and thermodynamic factors. Although some advances have been made with regard to the transamidation of primary amide substrates, secondary amide transamidation has remained elusive. Here we present a simple two-step approach that allows for the elusive overall transformation to take place using non-precious metal catalysis. The methodology proceeds under exceptionally mild reaction conditions and is tolerant of amino-acid-derived nucleophiles. In addition to overcoming the classic problem of secondary amide transamidation, our studies expand the growing repertoire of new transformations mediated by base metal catalysis.
Univ Calif Los Angeles
5/1/2016FALSEFALSEFALSECsp2-Nsp3E-NuNH
N(Me)Boc
H
Carbonyl
Morpholine
No baseNo Base_xx10.1021/acscatal.7b03688,10.1002/chem.201605095,10.1021/acs.orglett.7b00831,10.1021/acscatal.7b01444,10.1002/anie.201607856,10.1039/c7sc01980g,10.1021/acs.orglett.9b04497,10.1021/acs.orglett.6b02952,10.1002/anie.202103327,10.1002/chem.201702867,10.1055/s-0036-1588845,10.1021/acs.orglett.8b0102110.1002/anie.202200144,10.1021/acscatal.1c05738,10.1016/j.ceramint.2021.11.053,10.1039/d1ob02349g,10.1021/acs.joc.1c02245,10.1021/acs.joc.1c02245,10.15252/embr.202153135,10.1021/acs.orglett.1c03535,10.1002/ejoc.202101114,10.1021/acssuschemeng.1c05307,10.1021/acs.nanolett.1c02963,10.1080/00397911.2021.1989597,10.1016/j.tetlet.2021.153316,10.1002/tcr.202100224,10.1016/j.matt.2021.06.028,10.1039/d1ob01409a,10.1002/adom.202100850,10.1039/d1ob01021b,10.1002/bkcs.12371,10.1021/acs.orglett.1c01622,10.1021/acsami.1c08137,10.1039/d1ob00967b,10.1021/acsami.1c06140,10.1002/cctc.202100672,10.1021/acscatal.1c01840,10.1055/a-1517-5895,10.1002/anie.202103327,10.1016/j.nanoen.2021.106085,10.6023/cjoc202009048,10.1021/acs.orglett.1c01106,10.3866/PKU.WHXB202008051,10.1016/j.isci.2021.102168,10.1021/acs.joc.0c02868,10.1016/j.apcata.2021.118026,10.1021/acs.orglett.1c00010,10.1021/acs.orglett.0c04300,10.3389/fbioe.2021.613322,10.1021/acssuschemeng.0c08262,10.3390/molecules26010188,10.1039/d0sc05137c,10.1021/acs.orglett.0c03260,10.1039/d0cc04960c,10.1016/j.biotechadv.2020.107628,10.1039/d0ta07205b,10.1016/j.tetlet.2020.152444,10.1021/acscatal.0c03334,10.1016/j.tetlet.2020.152399,10.1039/d0qo00797h,10.3389/fbioe.2020.585935,10.1016/j.trechm.2020.08.001,10.1039/d0qo00713g,10.1055/s-0040-1707101,10.1055/s-0040-1705892,10.1016/j.jorganchem.2020.121359,10.1016/j.comptc.2020.112889,10.1039/d0ob01271h,10.1246/bcsj.20200116,10.1039/d0py00398k,10.1186/s13213-020-01562-z,10.1021/acs.orglett.0c00958,10.1016/j.biotechadv.2019.107497,10.1021/acscatal.9b05074,10.1021/acs.orglett.0c00885,10.1021/jacs.9b13531,10.1016/j.copbio.2019.07.005,10.1039/c9cy02486g,10.1021/acs.orglett.0c00485,10.1002/ejoc.201901730,10.1038/s41467-020-14799-8,10.1039/c9py01129c,10.1021/acs.orglett.9b04497,10.1039/c9cy02080b,10.1021/acs.joc.9b02826,10.1021/acs.orglett.9b03434,10.1002/tcr.201900072,10.1002/ejoc.201901396,10.1007/s00125-019-04973-z,10.1039/c9ob02096a,10.1002/ecm.1393,10.1055/s-0039-1690178,10.1002/adsc.201900819,10.1039/c9sc03440d,10.1039/c9cc05763c,10.1021/acs.joc.9b01699,10.1021/acs.joc.9b02013,10.1021/acs.joc.9b01103,10.1021/acs.orglett.9b02513,10.1002/ajoc.201900216,10.1021/jacs.9b03850,10.1007/s11426-019-9456-y,10.1002/anie.201803797,10.1002/adsc.201900485,10.1021/jacs.9b04136,10.1002/ejoc.201900666,10.1002/ejoc.201900531,10.1016/j.tet.2019.05.027,10.1039/c9nj01748h,10.1039/c9qo00106a,10.1002/ejoc.201900517,10.1002/ajoc.201900128,10.1021/acs.joc.9b00535,10.1021/acs.jchemed.8b00489,10.3390/molecules24071234,10.1021/acs.orglett.9b00554,10.1002/chem.201802635,10.1021/jacs.8b13251,10.1039/c8qo01052h,10.1055/s-0037-1610664,10.1016/j.dyepig.2018.09.070,10.1039/c8ob03010c,10.1016/j.jorganchem.2018.09.019,10.1021/acs.organomet.8b00720,10.1002/asia.201801317,10.1021/acs.orglett.8b03304,10.1016/j.biombioe.2018.09.033,10.1039/c8ob01832d,10.1039/c8cs00335a,10.1039/c8qo00591e,10.1038/s41467-018-06623-1,10.3390/molecules23102681,10.3390/molecules23102412,10.1021/acs.orglett.8b02303,10.1021/acs.oprd.8b00182,10.1021/acs.joc.8b00819,10.1021/acsenergylett.8b00764,10.1002/ajoc.201800258,10.1002/admi.201800301,10.1021/acs.orglett.8b01646,10.1246/cl.180361,10.1002/ejoc.201800109,10.1021/jacs.8b03739,10.1016/j.tetlet.2018.05.003,10.1073/pnas.1718373115,10.1021/acs.orglett.8b01021,10.1073/pnas.1714986115,10.1021/acs.joc.8b00160,10.1021/acs.orglett.8b00949,10.1021/acs.joc.8b00174,10.1073/pnas.1720810115,10.1016/j.tetlet.2018.01.097,10.1002/chem.201800336,10.1002/slct.201800048,10.1039/c7ob02874a,10.1021/acs.orglett.8b00080,10.1021/acscatal.7b03688,10.1055/s-0036-1590932,10.1007/s00253-018-8755-5,10.1021/acscatal.7b02599,10.1021/acsmacrolett.7b00896,10.1021/acs.orglett.7b03191,10.1055/s-0036-1589120,10.1016/j.biortech.2017.06.065,10.1021/jacs.7b09482,10.1007/s11426-017-9025-1,10.1039/c7cs00182g,10.1021/acs.orglett.7b02877,10.1021/acscatal.7b02859,10.1002/chem.201702867,10.1021/acs.orglett.7b02096,10.1039/c7sc02692g,10.1039/c7sc01980g,10.1055/s-0036-1588845,10.1002/chem.201702608,10.1021/acs.orglett.7b01575,10.1021/acscatal.7b01444,10.1038/natrevmats.2017.42,10.1021/acs.orglett.7b01194,10.1021/acs.joc.7b00971,10.1021/acs.orglett.7b01199,10.1126/science.aam9041,10.1002/anie.201703174,10.1002/chem.201605012,10.1021/acs.orglett.7b00831,10.1038/ncomms14993,10.1021/acs.orglett.7b00796,10.1021/acs.orglett.7b00429,10.1021/acs.orglett.7b00683,10.1002/anie.201611819,10.1002/crat.201700021,10.1002/anie.201612624,10.1021/acs.orglett.7b00373,10.1021/acscatal.6b03616,10.1021/acscatal.7b00245,10.1039/c7ob00086c,10.1021/acs.organomet.6b00769,10.1021/acscatal.6b03277,10.1021/jacs.6b12329,10.1021/acscatal.6b03040,10.1002/adsc.201600373,10.1002/chem.201605095,10.1021/acs.joc.6b02358,10.1021/acs.joc.6b02093,10.1021/acs.joc.6b02294,10.1002/anie.201607856,10.1021/acs.orglett.6b02952,10.1021/acscatal.6b02323,10.1021/acscatal.6b02333,10.1055/s-0036-1588080,10.1002/chem.201603543,10.1021/acs.orglett.6b01836,10.1021/acs.orglett.6b0175811/4/2021MAY2016FALSEFALSEFALSEFALSE7
350
195FALSEol302112q10.1021/ol302112qhttps://sci-hub.wf/10.1021/ol302112qhttps://doi.org/10.1021/ol302112qNiC-O ActivationShihongTRUE10712152012Prieto, A
Nickel-Catalyzed Amination of Aryl Sulfamates and Carbamates Using an Air-Stable Precatalyst
ORGANIC LETTERS
A facile nickel-catalyzed method to achieve the amination of synthetically useful aryl sulfamates and carbamates is reported. Contrary to most Ni-catalyzed amination reactions, this user-friendly approach relies on an air-stable Ni(II) precatalyst, which, when employed with a mild reducing agent, efficiently delivers aminated products in good to excellent yields. The scope of the method is broad with respect to both coupling partners and includes heterocyclic substrates.
Univ Huelva9/7/2012Csp2_ar-Csp2_arE-NuOMgOMeMgXArylArylNo baseNo BaseStrong-0.28_10.1246/cl.150936,10.1002/chem.201603436,10.1021/ol503707m,10.1021/ol502583h,10.1039/c4cc08187k,10.1002/ejic.201900692,10.1002/anie.201402922,10.1021/jacs.7b04973,10.1021/acscatal.7b01058,10.1021/acs.orglett.5b02200,10.1002/chem.201406457,10.1021/acs.organomet.5b0087410.1080/24701556.2021.2025075,10.1016/j.tetlet.2021.153388,10.1016/j.apmt.2021.101125,10.1039/c9cs00571d,10.1016/j.jcat.2020.12.016,10.1021/acs.joc.0c02389,10.1055/a-1349-3543,10.21577/0100-4042.20170701,10.1055/s-0040-1705986,10.1021/acsami.0c15192,10.1021/acs.chemrev.0c00088,10.1016/j.isci.2020.101377,10.1021/acs.joc.0c01277,10.1021/acs.joc.0c01381,10.1016/j.jorganchem.2020.121311,10.3390/catal10040372,10.1021/acs.joc.9b02933,10.1021/acs.joc.9b01113,10.1002/ejic.201900692,10.1016/j.ccr.2019.03.006,10.1002/cjoc.201800575,10.1021/acs.organomet.8b00878,10.1007/s00706-019-2364-6,10.1055/s-0037-1611663,10.1007/3418_2018_19,10.24820/ark.5550190.p010.866,10.1002/ajoc.201800560,10.1002/chem.201803297,10.1002/cctc.201800454,10.1039/c8dt01295d,10.1016/j.jorganchem.2018.01.019,10.1038/s41467-018-03928-z,10.1021/acs.orglett.8b00313,10.1016/j.tetlet.2018.02.008,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.24820/ark.5550190.p010.746,10.1039/c7ra12716b,10.1002/tcr.201700017,10.1021/jacs.7b04973,10.1248/cpb.c17-00487,10.1002/ejic.201700397,10.1039/c7dt01805c,10.1021/acscatal.7b01058,10.1002/ejic.201700057,10.1021/acs.organomet.7b00109,10.1039/c6qo00533k,10.1002/anie.201609635,10.1039/c6dt03241a,10.1002/chem.201603436,10.1021/acs.orglett.6b02631,10.1021/acs.orglett.6b02550,10.1002/asia.201600972,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acs.orglett.5b03712,10.1007/s40242-016-5261-0,10.1016/bs.adomc.2016.07.001,10.1002/jhet.2394,10.1021/acs.organomet.5b00874,10.1246/cl.150936,10.1021/jacs.5b08621,10.1002/ejoc.201500987,10.1002/chem.201502114,10.1021/acs.orglett.5b02200,10.1021/acs.orglett.5b01229,10.1055/s-0034-1380813,10.1016/j.tet.2015.02.088,10.1016/j.ccr.2014.12.019,10.1021/acs.accounts.5b00051,10.1016/j.ica.2014.11.005,10.1002/aoc.3289,10.1002/adsc.201500030,10.1002/chem.201406457,10.1021/ol503707m,10.1021/cs5014927,10.1055/s-0034-1378914,10.1039/c5qo00001g,10.1039/c4cc08012b,10.1039/c4cc08187k,10.1039/c5ra12512j,10.1246/bcsj.20140241,10.1002/ejoc.201403125,10.1002/anie.201402922,10.1021/ol502583h,10.1016/j.jscs.2014.02.002,10.1002/anie.201403288,10.1021/ol403631k,10.1021/jo4024123,10.1039/c4ob00677a,10.1039/c4cs00206g,10.1039/c4dt00461b,10.1016/j.tetlet.2013.10.071,10.1021/ol402262c,10.1002/ejoc.201300750,10.1002/ejoc.201300850,10.1021/ja404006w,10.1002/ejoc.201300347,10.1039/c3dt00086aKelly11/25/2021
351
371FALSEjo00199a03010.1021/jo00199a030https://sci-hub.wf/10.1021/jo00199a030https://doi.org/10.1021/jo00199a030NiDeletedLongFALSE22637691984WENKERT, E#N/ATRANSFORMATION OF CARBON OXYGEN INTO CARBON CARBON BONDS MEDIATED BY LOW-VALENT NICKEL SPECIESJ ORG CHEM
UNIV CALIF SAN DIEGO,DEPT CHEM,LA JOLLA,CA 92093
12/1/1984_10.1021/acs.orglett.5b02200,10.1021/ol203322v,10.1021/ol901978e,10.1021/ja210249h,10.1002/anie.200907287,10.1002/chem.201003731,10.1039/b718998b,10.1021/ol4011757,10.1021/ol4031815,10.1021/ol503707m,10.1021/acs.organomet.5b00874,10.1002/anie.201402922,10.1021/jacs.8b02134,10.1021/ol9028308,10.1021/ja710944j,10.1021/ol302112q,10.1002/anie.200907359,10.1021/acscatal.7b01058,10.1021/jo00205a042,10.1246/cl.2009.710,10.1021/ol502583h,10.1002/chem.201603436,10.1021/jo2000034,10.1002/anie.202012048,10.1002/anie.200900329,10.1246/cl.150936,10.1002/chem.201103784,10.1002/anie.201607646,10.1021/ja903091g,10.1002/anie.200803814,10.1021/acscatal.6b00801,10.1016/j.tet.2012.04.005,10.1002/chem.200902785,10.1002/chem.201505106,10.1021/ja8056503,10.1021/ja810157e,10.1039/c4cc08187k10.1039/d1ra08771a,10.1007/s13738-021-02350-5,10.1021/acscatal.1c01077,10.1039/d1gc00141h,10.1055/a-1349-3543,10.1055/s-0040-1705986,10.1002/anie.202012048,10.1021/acs.orglett.0c03507,10.1021/acscatal.0c03334,10.1021/acs.chemrev.0c00088,10.1002/cjoc.201900506,10.1021/jacs.0c00359,10.1021/acs.orglett.9b03170,10.3390/inorganics7100121,10.1007/s13738-019-01615-4,10.1039/c9sc01083a,10.1002/cjoc.201800575,10.1021/acs.orglett.9b00946,10.1055/s-0037-1611663,10.1007/3418_2018_19,10.1021/acs.accounts.8b00408,10.1002/chem.201803451,10.1039/c8cc03665a,10.1002/anie.201802434,10.1039/c8cc02325e,10.1021/acs.orglett.8b00755,10.1038/s41467-018-03928-z,10.1021/acs.orglett.8b00313,10.1021/jacs.8b02134,10.1002/ajoc.201700450,10.1002/cjoc.201700664,10.1002/chem.201703266,10.1002/ejoc.201701197,10.1248/cpb.c17-00487,10.1021/acscatal.7b01058,10.1039/c6sc02895k,10.1021/acscatal.6b02964,10.1002/anie.201607646,10.1002/chem.201603436,10.1002/asia.201600972,10.1002/chem.201602150,10.1007/s41061-016-0043-1,10.1021/acscatal.6b00801,10.1002/chem.201505106,10.1016/bs.adomc.2016.07.001,10.1021/acscatal.5b02089,10.1021/acs.organomet.5b00874,10.1246/cl.150936,10.1021/acs.organomet.5b00710,10.1021/acs.orglett.5b01913,10.1002/chem.201502114,10.1021/acs.orglett.5b02200,10.1002/ejoc.201500630,10.1021/acs.orglett.5b01229,10.1002/adsc.201500304,10.1021/acs.orglett.5b00654,10.1021/ar500345f,10.1021/ja512498u,10.1021/ol503707m,10.1039/c5qo00001g,10.1039/c5nj01354b,10.1039/c4cc08187k,10.1002/anie.201402922,10.1021/ol502583h,10.1002/adsc.201400624,10.1055/s-0034-1379210,10.1021/ja503819x,10.1021/ic500258g,10.1021/ja5043534,10.1515/pac-2014-5038,10.1016/j.tetlet.2013.12.083,10.1021/om401204h,10.1039/c4cs00206g,10.1002/ejoc.201301372,10.1021/ol4031815,10.1002/anie.201307028,10.6023/cjoc201301073,10.1021/ol4011757,10.1021/ja312464b,10.1016/j.tetlet.2012.12.027,10.1007/3418_2012_42,10.1039/c3cs35521g,10.1002/ejoc.201200914,10.1039/c3ra44884c,10.1021/ol302112q,10.1016/j.tet.2012.04.005,10.1021/ol3009842,10.1021/ol203322v,10.1021/ol3000519,10.1002/chem.201103784,10.1021/ja210249h,10.1039/c2cc34454h,10.1002/anie.201203778,10.1039/c1cc15845g,10.1021/ja207759e,10.1246/cl.2011.1001,10.1021/ol201069x,10.1021/ol2012007,10.1126/science.1200437,10.1002/chem.201003731,10.1021/jo2000034,10.1002/chem.201002386,10.1021/cr100259t,10.1021/jo102338a,10.1002/anie.201100293,10.1002/anie.201103599,10.1039/c0cc05169a,10.1002/chem.201002273,10.1021/ar100082d,10.1002/adsc.201000350,10.1021/ol1018739,10.1021/jo1007898,10.1021/ol9028308,10.1002/anie.200907287,10.1002/anie.200907359,10.1002/chem.200902785,10.1039/b920285d,10.1021/ol901978e,10.1021/ja903091g,10.1055/s-0029-1216832,10.1246/cl.2009.710,10.1021/ja810157e,10.1021/ol802865c,10.1002/ejoc.200801174,10.1002/anie.200900329,10.1021/ja8056503,10.1016/j.tetlet.2008.08.002,10.1016/j.tetlet.2008.04.117,10.1021/jm701390c,10.1021/ja710944j,10.1002/anie.200801447,10.1002/anie.200803814,10.1039/b718998b,10.1002/ejoc.200700312,10.1002/anie.200604629,10.1021/ja067612p,10.1016/j.molcata.2006.06.004,10.1055/s-2006-939682,10.1016/j.jorganchem.2005.09.010,10.1055/s-2005-871571,10.1016/j.jorganchem.2004.10.037,10.1055/s-2004-831247,10.1002/anie.200462280,10.1002/anie.200462672,10.1055/s-2004-834878,10.1016/j.tet.2004.03.072,10.1021/ja0393170,10.1016/S0040-4039(03)01804-5,10.1055/s-2003-41008,10.1016/S0957-4166(00)00361-X,10.1016/S0040-4020(99)01095-9,10.1021/jo991196s,10.1016/S0040-4039(99)01975-9,10.1016/S0040-4039(98)00513-9,10.1016/S0040-4020(97)10233-2,10.1039/a607663g,10.1016/0957-4166(96)00391-6,10.1021/jo9516852,10.1016/0957-4166(95)00371-1,10.5059/yukigoseikyokaishi.51.894,10.1021/jo00057a055,10.1039/p19920003431,10.1016/S0040-4020(01)88230-2,10.1016/0022-328X(92)83346-J,10.1080/00397919208021314,10.1016/S0040-4039(00)79422-6,10.1016/S0040-4039(00)92687-X,10.1021/jo00002a028,10.1021/jo00309a008,10.1016/0040-4039(90)80134-8,10.1021/ja00188a095,10.1021/jo00266a047,10.1021/jo00248a016,10.1021/ar00146a001,10.1016/S0040-4020(01)86177-9,10.1016/S0040-4039(00)86058-X,10.1016/S0040-4039(00)86059-1,10.1021/jo00392a020,10.1039/c39870000241,10.1021/ja00271a037,10.1002/cber.19861190324,10.1080/00397918608056418,10.1021/jo00205a042,10.1021/jo00220a029Kelly#N/A
352
372FALSEja308942210.1021/ja3089422https://sci-hub.wf/10.1021/ja3089422https://doi.org/10.1021/ja3089422NiC-N ActivationLongTRUE10822272013Watson, MP
Nickel-Catalyzed Cross Couplings of Benzylic Ammonium Salts and Boronic Acids: Stereospecific Formation of Diarylethanes via C-N Bond Activation
J AM CHEM SOC
We have developed a nickel-catalyzed cross coupling of benzylic ammonium triflates with aryl boronic acids to afford diarylmethanes and diarylethanes. This reaction proceeds under mild reaction conditions and with exceptional functional group tolerance. Further, it transforms branched benzylic ammonium salts to diarylethanes with excellent chirality transfer, offering a new strategy for the synthesis of highly enantioenriched diarylethanes from readily available chiral benzylic amines.
Univ Delaware1/9/2013TRUETRUEFALSEyyCsp2_ar-Csp2_arE-NuNB
NMe3+OTf-
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c02923b,10.1039/c4cc05376a,10.1002/chem.201303683,10.1016/j.tet.2013.09.039,10.1021/ja408561b,10.1002/ejoc.201300594,10.1021/ja4076716,10.1007/s11426-013-4880-2,10.1007/s40242-013-3057-z,10.1021/ol400295z,10.1021/ol400289v,10.1021/ja312087x11/1/2021JAN 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353
373FALSEja509534210.1021/ja5095342https://sci-hub.wf/10.1021/ja5095342https://doi.org/10.1021/ja5095342NiC-H ActivationGerry14-FebTRUE6216892014Chatani, N
Ni(II)-Catalyzed Oxidative Coupling between C(sp(2))-H in Benzamides and C(sp(3))-H in Toluene Derivatives
J AM CHEM SOC
Oxidative coupling between C((sp2)))-H bonds and C((sp3)))-H bonds is achieved by the Ni(II)-catalyzed reaction of benzamides containing an 8-aminoquinoline moiety as the directing group with toluene derivatives in the presence of heptafluoroisopropyl iodide as the oxidant. The method has a broad scope and shows high functional group compatibility. Toluene derivatives can be used as the coupling partner in an unreactive solvent.
Osaka Univ11/5/2014TRUETRUEFALSEyCsp2_ar-Csp3-ring(s)E-NuCsp3HCH3HArylBenzylNo baseNo Base_xx10.1021/acscatal.7b01044,10.1039/c5cc01436k,10.1021/acs.organomet.6b00201,10.1039/d1cc02983e,10.1246/bcsj.20140387,10.1002/anie.201510743,10.1021/acs.organomet.6b00529,10.1038/ncomms9404,10.1021/acscatal.6b01120,10.1002/ajoc.201700569,10.1039/c5sc02942b,10.1039/c9sc01446b,10.1021/acs.orglett.6b02236,10.1021/acs.joc.5b00669,10.1021/acs.orglett.6b00658,10.1039/c6qo00149a10.1002/adsc.202100992,10.1016/j.tet.2021.132415,10.1021/acscatal.1c03314,10.1021/acs.orglett.1c02567,10.1002/chem.202101004,10.1039/d1cc02983e,10.1039/d1qo00727k,10.1002/tcr.202100113,10.1016/j.ijhydene.2021.03.213,10.1021/acs.organomet.1c00265,10.1021/acs.orglett.1c01129,10.1016/j.tetlet.2021.152872,10.1016/j.tetlet.2021.152950,10.1055/a-1422-9632,10.1002/adsc.202001498,10.1016/j.tetlet.2021.152825,10.1002/ajoc.202100006,10.2174/1385272825666210608114300,10.1021/acs.joc.0c02069,10.1021/acs.orglett.0c03535,10.1016/j.renene.2020.07.089,10.1021/acs.orglett.0c01867,10.1039/d0qo00587h,10.1021/acs.joc.0c00788,10.1002/adsc.202000280,10.1002/anie.202004958,10.1002/adsc.202000199,10.1055/s-0037-1610756,10.1080/00397911.2020.1761392,10.1021/jacs.0c00169,10.1002/cjoc.201900468,10.1021/acs.joc.0c00466,10.1021/acs.orglett.0c00588,10.1021/acs.chemrev.9b00495,10.1002/adsc.201901158,10.1002/anie.201903726,10.1002/zaac.201900093,10.1002/ajoc.201900554,10.1039/c9sc03758f,10.1016/j.tetlet.2019.151225,10.1039/c9sc01446b,10.1039/c9ob01919g,10.1021/acs.joc.9b01775,10.1002/tcr.201800093,10.1039/c9qo00644c,10.1016/j.trechm.2019.06.002,10.1002/adsc.201900370,10.1002/anie.201808159,10.1021/jacs.9b02411,10.1039/c9ob00449a,10.1002/anie.201806629,10.1021/acs.joc.9b00237,10.1002/cctc.201900254,10.1038/s41929-019-0245-3,10.1038/s41467-019-09857-9,10.1039/c9cc01060b,10.1021/acs.organomet.8b00899,10.1002/asia.201900050,10.3390/molecules24071234,10.1039/c8sc05063e,10.1038/s42004-019-0132-5,10.1021/acsomega.9b00030,10.1039/c8qo01290c,10.1002/cctc.201801625,10.1039/c9ra00749k,10.1055/s-0037-1610342,10.1039/c8ob02237b,10.1002/chem.201804415,10.1016/j.tetlet.2018.10.010,10.1021/acs.orglett.8b02812,10.1021/acs.joc.8b01807,10.1021/jacs.8b05143,10.1021/jacs.8b07708,10.1055/s-0037-1610906,10.1039/c8ob01712c,10.1039/c8ob01481g,10.1021/acscatal.8b02361,10.1039/c8cc04679d,10.1021/jacs.8b05240,10.1021/acscatal.8b01675,10.1021/acs.orglett.8b01382,10.1002/ejic.201800168,10.1016/j.tetlet.2018.04.036,10.1002/anie.201711291,10.1055/s-0036-1591748,10.1039/c7sc04604a,10.1098/rsos.171870,10.5059/yukigoseikyokaishi.76.11,10.1016/bs.adomc.2018.02.002,10.1039/c8ra01377b,10.1002/ajoc.201700569,10.1021/acs.organomet.7b00613,10.1021/acs.orglett.7b02968,10.1002/ijch.201700044,10.1021/acs.orglett.7b02823,10.1002/chem.201704045,10.1039/c7cc05532c,10.1055/s-0036-1588487,10.1039/c7sc01750b,10.1055/s-0036-1588160,10.1021/acs.joc.7b01137,10.1038/s41467-017-00078-6,10.1021/acs.orglett.7b01529,10.1021/jacs.7b03548,10.1002/chem.201605657,10.1021/jacs.7b03387,10.1021/acscatal.7b01072,10.1021/acscatal.7b01044,10.1002/cssc.201700321,10.1039/c7cc01423f,10.1039/c7sc00250e,10.1021/acscatal.7b00247,10.1021/acs.orglett.7b00479,10.1039/c6sc05581h,10.1021/acs.orglett.7b00116,10.1039/c6sc05026c,10.1039/c6qo00522e,10.1021/acs.orglett.6b03856,10.1002/chem.201605188,10.1002/ejoc.201601151,10.1021/jacs.6b10303,10.1021/acs.organomet.6b00529,10.1039/c6qo00529b,10.1021/acs.joc.6b02353,10.1021/jacs.6b10350,10.1002/ajoc.201600389,10.1021/acscatal.6b02186,10.1007/s40010-016-0289-6,10.1021/acs.organomet.6b00655,10.1021/acscatal.6b02477,10.1016/j.jorganchem.2016.08.026,10.1021/jacs.6b06862,10.1002/anie.201606529,10.1021/acs.orglett.6b02236,10.1016/j.jfluchem.2016.07.021,10.1021/acs.inorgchem.6b01162,10.1021/acscatal.6b01816,10.1002/adsc.201600378,10.1002/adsc.201600177,10.1021/acscatal.6b01120,10.1055/s-0035-1561946,10.1021/acscatal.6b00964,10.1021/acs.organomet.6b00201,10.1002/anie.201601296,10.1002/adsc.201600080,10.1021/acs.joc.6b00129,10.1002/chem.201600229,10.1021/acs.orglett.6b00566,10.1021/acs.orglett.6b00749,10.1021/acs.orglett.6b00658,10.1021/acs.orglett.5b02472,10.1002/anie.201510743,10.1021/jacs.6b00250,10.1002/adsc.201500791,10.1007/3418_2015_117,10.1039/c6qo00149a,10.1039/c6ra07450b,10.1039/c5cc10084d,10.1039/c6cc00822d,10.1039/c6qo00158k,10.1021/acs.joc.5b02264,10.1021/acs.orglett.5b03142,10.1021/cr500431s,10.1002/chem.201503511,10.1021/acs.orglett.5b03059,10.1002/adsc.201500632,10.1002/asia.201500599,10.1021/acs.organomet.5b00733,10.1038/srep15250,10.1246/cl.150615,10.1021/jacs.5b07432,10.1021/acs.organomet.5b00581,10.1021/acs.orglett.5b01955,10.1002/ajoc.201500105,10.1038/ncomms9404,10.1055/s-0034-1381031,10.1002/chem.201501962,10.1246/cl.150239,10.1002/chem.201500639,10.1021/acs.joc.5b00669,10.1021/acs.orglett.5b01185,10.1246/cl.150041,10.1021/acs.joc.5b00580,10.1021/jacs.5b01671,10.1246/cl.150024,10.1246/bcsj.20140387,10.1021/acs.orglett.5b00337,10.1021/ja5116452,10.1039/c5cc05527j,10.1039/c5ob01763g,10.1039/c5sc02942b,10.1039/c5sc01636c,10.1039/c5cc04791a,10.1039/c5cc03729h,10.1039/c5dt00032g,10.1039/c5cc02254a,10.1039/c5cc01436k,10.1039/c5cc01163a,10.1039/c5ra02242h,10.1039/c4cc09594d,10.1039/c4cc10431e,10.1039/c4cc08797f,10.1039/c4cc10015h,10.1039/c4cc10446c,10.1039/c5cs00003c11/14/2021NOV 52014FALSEFALSEFALSEFALSE1364415509
354
89FALSEol401175710.1021/ol4011757https://sci-hub.wf/10.1021/ol4011757https://doi.org/10.1021/ol4011757NiC-O ActivationKellyTRUE4910282013Shi, ZJ
Kumada-Tamao-Corriu Coupling of Heteroaromatic Chlorides and Aryl Ethers Catalyzed by (IPr)Ni(allyl)Cl
ORGANIC LETTERS
The complex (IPr)Ni(allyl)Cl (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazolidene) catalyzes the cross-coupling reactions of heteroaromatic chlorides with aryl Grignard reagents. Catalyst loadings as low as 0.1 mol % have been used to afford the products in excellent yields. This nickel-based catalytic system also promotes the activation of the C-Ar-O bond of anisoles in the Kumada-Tamao-Corriu reaction under fairly mild conditions.
Peking Univ7/5/2013TRUETRUETRUECsp2_ar-Csp2_arE-NuOB
OCONEt2
B(OH)2ArylArylK2CO3Ionic-CO3Medium0.31_shihong added10.1002/chem.201603436,10.1021/ol503707m,10.1021/ol502583h,10.1246/cl.150936,10.1021/om500452c,10.1002/anie.201806790,10.1021/acs.orglett.5b02200,10.1039/c4qo00321g,10.1021/acs.organomet.5b00874,10.1021/acscatal.6b0080110.6023/cjoc202104056,10.1039/d1qo00549a,10.1039/d0ra08068c,10.1021/acscatal.0c03334,10.1021/acs.chemrev.0c00088,10.1246/cl.200190,10.2174/1385272824666200211114540,10.1039/c9gc02694k,10.1021/acs.orglett.9b02504,10.1021/acs.orglett.9b00875,10.1002/slct.201803626,10.1002/anie.201806790,10.1002/cjoc.201700773,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.1016/j.tetlet.2017.06.055,10.1016/j.tetlet.2016.11.035,10.1021/acs.orglett.6b03306,10.1002/chem.201603436,10.1002/asia.201600972,10.1021/acssuschemeng.6b00729,10.1021/acscatal.6b00801,10.1002/adsc.201600205,10.1002/chem.201503090,10.1016/bs.adomc.2016.07.001,10.1021/acs.organomet.5b00874,10.1002/cctc.201500575,10.1246/cl.150936,10.1021/jacs.5b08621,10.1002/chem.201502418,10.1002/chem.201502114,10.1021/acs.orglett.5b02200,10.1021/acs.orglett.5b00353,10.1021/ol503707m,10.1039/c4qo00321g,10.1039/c5qo00039d,10.1039/c5ra13137e,10.1021/ol502583h,10.1016/j.ica.2014.08.012,10.1021/om500452c,10.1002/chem.201404380,10.1055/s-0033-1339114,10.1002/ejoc.201400090,10.1002/anie.201309546,10.1039/c4cs00206g,10.1016/j.tet.2013.09.060,10.1039/c3ra44884c Long 11/9/2021
355
197FALSEol401727y10.1021/ol401727yhttps://sci-hub.wf/10.1021/ol401727yhttps://doi.org/10.1021/ol401727yNiC-O ActivationLongTRUE1108542013Garg, NK
Programmed Selective sp(2) C-O Bond Activation toward Multiarylated Benzenes
ORGANIC LETTERS
A variety of important multiarylated benzenes were efficiently synthesized from phloroglucinol derivatives 1 through sequential cross-couplings via Pd-catalyzed C-OTs, Ni-catalyzed C-OC(O)NEt2, and C-OMe bond activation. High selectivity was achieved based on the rational design and inherent diversity in the reactivity of different C-O bonds.
Univ Calif Los Angeles
8/2/2013Csp2_ar-Csp2_arE-NuOB
OSO2NMe2
B(OH)2ArylArylK3PO4Ionic-PO4Weak0.36_10.1039/c7cc06717h,10.1021/ja5029793,10.1021/acscatal.9b00744,10.1021/jacs.6b11412,10.1021/acs.orglett.6b01398,10.1021/cs501045v,10.1021/jacs.7b04973,10.1021/acs.joc.6b0162710.1016/j.scp.2021.100551,10.1039/d1sc04582b,10.1039/d1ob01765a,10.1021/acscatal.1c02790,10.6023/cjoc202007059,10.1021/acs.chemrev.0c00709,10.17344/acsi.2021.6920,10.3987/COM-21-14540,10.1021/acscatal.0c03888,10.1021/acs.chemrev.0c00088,10.1021/acsomega.0c03415,10.1007/s11030-019-09988-7,10.1039/d0ra02195d,10.1021/acs.joc.0c00530,10.1002/cssc.202000317,10.3762/bjoc.16.89,10.1021/acs.jchemed.9b00753,10.1039/c9cp06802c,10.1039/c9ob02408e,10.1021/acs.organomet.9b00672,10.6023/cjoc201908020,10.1002/asia.201901442,10.1016/j.molliq.2019.111454,10.1016/j.jcat.2019.07.026,10.1002/aoc.4831,10.1021/acscatal.9b00744,10.1002/slct.201900153,10.1016/j.tet.2019.01.015,10.1039/c8gc02860e,10.1016/j.molstruc.2018.09.064,10.1007/3418_2018_19,10.1002/cctc.201801350,10.1039/c8gc01276h,10.1021/acs.jpcc.8b07538,10.1002/cssc.201801382,10.1021/acs.oprd.8b00237,10.1002/cssc.201801641,10.1002/adsc.201800729,10.1039/c8ob01034j,10.1021/acs.orglett.8b01520,10.1055/s-0037-1610024,10.1016/j.jorganchem.2018.01.019,10.1016/j.jorganchem.2018.02.030,10.1055/s-0036-1591523,10.1055/s-0036-1589143,10.1002/adsc.201701115,10.1039/c7cc06717h,10.1055/s-0036-1590985,10.1021/acs.organomet.7b00642,10.1021/jacs.7b04973,10.1039/c7cc05000c,10.1002/anie.201704948,10.1002/ajoc.201700218,10.1002/slct.201700580,10.1021/acs.jchemed.6b00273,10.1039/c7gc00067g,10.1038/s41570-017-0025,10.1007/s10847-016-0673-5,10.1021/acscatal.6b03277,10.1021/jacs.6b11412,10.1007/s00706-016-1879-3,10.1021/acs.orglett.6b02330,10.1021/acs.joc.6b01627,10.1007/s12274-016-1176-9,10.1002/aoc.3507,10.1002/chem.201602668,10.1002/adsc.201600590,10.1021/acs.orglett.6b01398,10.1039/c6dt01183g,10.1039/c6gc00932h,10.1039/c5nj02734a,10.1039/c5gc01869b,10.1002/adsc.201500685,10.1021/acs.joc.5b01681,10.1002/anie.201505136,10.1007/s10562-015-1558-8,10.1016/j.jorganchem.2015.03.007,10.1021/ed500158p,10.1039/c5qo00093a,10.1039/c4ob02586e,10.2174/157017941206150828102108,10.1016/j.catcom.2014.08.010,10.1021/ja5099935,10.1016/j.ica.2014.08.012,10.1021/jo501615a,10.1021/ol502042r,10.1021/cs501045v,10.1016/j.tetlet.2014.06.114,10.1021/sc5002287,10.1021/ja5029793,10.1038/nature13274,10.1021/om5001327,10.1021/ja4118413,10.1039/c4ob00978a,10.1039/c4ob00575a,10.1039/c3ob41382a,10.1021/ja409803xKelly12/15/2021
356
376FALSEanie.20130958410.1002/anie.201309584https://sci-hub.wf/10.1002/anie.201309584https://doi.org/10.1002/anie.201309584NiC-H ActivationElaine8-FebTRUE2291932014
Ackermann, L
Nickel-Catalyzed C-H Alkylations: Direct Secondary Alkylations and Trifluoroethylations of Arenes
ANGEW CHEM INT EDIT
A versatile nickel catalyst allowed for C-H alkylations of unactivated arenes with challenging secondary alkyl bromides and chlorides. The high catalytic efficacy also set the stage for direct secondary alkylations of indoles as well as C-H trifluoroethylations with ample substrate scope.
Univ Gottingen2/24/2014TRUEFALSEFALSECsp2_ar-Csp3E-NuXHBrHArylAlkylLiOtBuIonic-OtBu_10.1039/c9sc01446b,10.1021/acscatal.6b01120,10.1021/acs.joc.5b00669,10.1039/d1cc02983e,10.1021/acscatal.6b02003,10.1021/acs.orglett.6b02236,10.1021/acscatal.7b01044,10.1039/c5cc01436k,10.1039/c5sc03704b,10.1246/bcsj.20140387,10.1002/anie.201709087,10.1021/acs.orglett.6b02166,10.1039/c5cy01299f,10.1002/ajoc.201700569,10.1039/c5sc01589h,10.1021/acs.organomet.6b00201,10.1002/anie.201510743,10.1021/ol501707z,10.1039/c6qo00149a10.1002/chem.202103599,10.6023/cjoc202104007,10.1039/d1cc03589d,10.1039/d1nj01696b,10.1039/d1cc02983e,10.1039/d1ra03992j,10.1002/tcr.202100113,10.1039/d1cc02007b,10.1016/j.tetlet.2021.152872,10.1039/d1qo00210d,10.1002/ajoc.202000712,10.1021/acscatal.0c05580,10.1016/j.tetlet.2021.152825,10.1021/acs.orglett.1c00058,10.1021/acs.joc.0c02739,10.1016/j.jscs.2020.101178,10.1021/acs.orglett.0c03418,10.1002/adsc.202000985,10.1021/acs.orglett.0c02609,10.1021/acs.chemrev.9b00682,10.1021/acs.orglett.0c01700,10.1016/j.chempr.2020.04.006,10.1002/anie.202004958,10.1055/s-0037-1610756,10.1080/00397911.2020.1761392,10.1002/cjoc.201900468,10.1246/cl.200015,10.1002/ajoc.202000124,10.1002/ejoc.201901929,10.1021/acs.chemrev.9b00495,10.1002/adsc.201901405,10.2174/1385272824999200616114037,10.1021/acs.accounts.9b00510,10.1016/j.tetlet.2019.151396,10.1002/ajoc.201900554,10.1002/adsc.201901119,10.1039/c9cc06822h,10.1039/c9sc01446b,10.1002/tcr.201800093,10.1002/chem.201902818,10.1016/j.tet.2019.05.047,10.1016/j.trechm.2019.06.002,10.1039/c9ra03421h,10.1021/acs.orglett.9b01846,10.1021/acs.joc.9b00470,10.6023/cjoc201901015,10.1002/anie.201806629,10.1002/ajoc.201900030,10.1039/c9ob00243j,10.1039/c9cy00009g,10.1021/acs.organomet.8b00899,10.1039/c8sc05063e,10.1021/acs.orglett.9b00351,10.1039/c8qo01274a,10.1021/acsomega.9b00030,10.1021/acscatal.8b04872,10.1055/s-0037-1611633,10.1021/acs.chemrev.8b00068,10.1021/acs.chemrev.8b00507,10.1002/cctc.201801625,10.1002/anie.201813191,10.1007/s00706-018-2305-9,10.1002/chem.201805441,10.1039/c8ob02237b,10.1038/s42004-018-0092-1,10.1021/acscatal.8b03770,10.1021/acs.orglett.8b02736,10.1021/acs.orglett.8b02699,10.1039/c8ob01481g,10.1039/c8cc05026k,10.1039/c8ob00645h,10.1021/acs.joc.8b00174,10.1002/slct.201800679,10.1021/acs.organomet.8b00025,10.1039/c7sc04604a,10.1039/c8ra03278e,10.1039/c8ra01377b,10.1002/ajoc.201700569,10.1039/c7dt03403b,10.1002/anie.201709087,10.1016/j.jfluchem.2017.09.009,10.1021/acs.orglett.7b02968,10.1139/cjc-2017-0258,10.1039/c7cc05532c,10.1039/c7ob01791j,10.1039/c7sc01750b,10.1002/chem.201703191,10.1039/c7cc05011a,10.1021/acs.orglett.7b01859,10.1002/adsc.201700186,10.1039/c7sc01732d,10.1039/c7qo00211d,10.1021/jacs.7b03548,10.1002/chem.201605657,10.1002/adsc.201700290,10.1021/acscatal.7b01044,10.1002/cssc.201700321,10.1021/acs.orglett.7b00730,10.1016/j.tetlet.2017.02.090,10.1055/s-0036-1588936,10.1021/acscatal.7b00247,10.1039/c6sc05622a,10.1039/c7cc01097d,10.1039/c7cc01201b,10.1039/c7cc01274h,10.1002/ajoc.201600596,10.1016/j.tetlet.2017.01.060,10.1021/acs.joc.6b02797,10.1002/adsc.201601136,10.1016/j.tetlet.2016.11.015,10.1007/s40010-016-0289-6,10.1016/j.jorganchem.2016.08.025,10.1002/chem.201604344,10.6023/A16060316,10.1021/acs.joc.6b01702,10.1021/acs.orglett.6b02166,10.1021/acs.orglett.6b02236,10.1002/chem.201603092,10.1021/acscatal.6b02003,10.1021/acs.joc.6b00950,10.1021/acs.inorgchem.6b01162,10.1021/acscatal.6b01816,10.1007/s41061-016-0053-z,10.1002/adsc.201600177,10.1021/acscatal.6b01120,10.1002/chem.201600293,10.1021/acs.organomet.6b00201,10.1002/adsc.201600080,10.1021/jacs.6b02405,10.1016/j.jfluchem.2016.03.007,10.1002/anie.201511954,10.1002/anie.201510743,10.1002/anie.201510555,10.1021/acscatal.5b02344,10.1002/anie.201509603,10.1007/3418_2015_117,10.1039/c6ob01856d,10.1039/c6qo00149a,10.1039/c6ob01384h,10.1039/c6cc90302a,10.1039/c6ra07450b,10.1039/c5cy01299f,10.1039/c5ob02363g,10.1039/c5sc03704b,10.1039/c6cc00822d,10.1039/c6ob00164e,10.1021/acs.orglett.5b03142,10.1055/s-0035-1560260,10.1021/acs.orglett.5b02678,10.1021/acs.organomet.5b00504,10.1021/acs.organomet.5b00405,10.1021/acs.orglett.5b02177,10.1021/jacs.5b08914,10.1016/j.jorganchem.2015.03.023,10.1021/acs.organomet.5b00581,10.1021/jacs.5b07507,10.1002/ajoc.201500105,10.1021/acscatal.5b01075,10.1002/anie.201504735,10.1002/anie.201501926,10.1246/cl.150239,10.1055/s-0034-1379927,10.1016/j.tetlet.2015.05.025,10.1016/j.tet.2015.03.066,10.1002/chem.201500639,10.1021/acs.joc.5b00669,10.1002/chem.201501134,10.1021/acs.orglett.5b01232,10.1021/acs.orglett.5b00990,10.1002/anie.201412026,10.1021/jacs.5b01671,10.1002/chem.201500552,10.1246/cl.150024,10.1021/ar5004626,10.1021/jacs.5b01365,10.1246/bcsj.20140387,10.1002/adsc.201400947,10.1021/acs.orglett.5b00155,10.1002/chem.201405942,10.1055/s-0034-1379247,10.1002/anie.201410471,10.1021/ja511557h,10.1002/anie.201409751,10.1039/c5qo00167f,10.1039/c5sc01589h,10.1039/c5ob00149h,10.1039/c5cc01970b,10.1039/c5cc02254a,10.1039/c5cc01436k,10.1039/c5cc01163a,10.1039/c5cc00519a,10.1039/c4cc10431e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242014FALSEFALSEFALSEFALSE5392477
357
118FALSEol403136410.1021/ol4031364https://sci-hub.wf/10.1021/ol4031364https://doi.org/10.1021/ol4031364NiC-O ActivationShihongTRUE606452014Doyle, AG
Nickel-Catalyzed Suzuki-Miyaura Couplings in Green Solvents
ORGANIC LETTERS
The nickel-catalyzed Suzuki-Miyaura coupling of aryl halides and phenol-derived substrates with aryl boronic acids using green solvents, such as 2-Me-THF and tert-amyl alcohol, is reported. This methodology employs the commercially available and air-stable precatalyst, NiCl2(PCy3)(2), and gives biaryl products in synthetically useful to excellent yields. Using this protocol, bis(heterocyclic) frameworks can be assembled efficiently.
Princeton Univ1/3/2014Csp2_ar-Csp2_arE-NuOBOEtB(OH)2HetArylIonic-ORStrong-0.24_10.1039/c7sc05216b,10.1039/c6sc00702c,10.1038/NCHEM.2741,10.1021/jacs.6b11412,10.1002/anie.201507494,10.1021/ol503061c10.1039/d1sc05605k,10.1002/ejic.202100820,10.6023/cjoc202106021,10.1021/acscatal.1c03449,10.1039/c9cs00571d,10.1002/aoc.6158,10.1021/acs.organomet.9b00834,10.1021/acs.orglett.0c01109,10.1021/acs.orglett.9b04220,10.1021/acs.orglett.9b03633,10.1016/j.jorganchem.2019.120937,10.1002/ejoc.201900566,10.1021/acs.orglett.9b02034,10.1002/anie.201903377,10.1039/c9sc00554d,10.1021/jacs.9b00615,10.1002/chir.23036,10.6023/cjoc201809037,10.1016/j.tet.2018.03.039,10.1039/c7sc05216b,10.1002/adsc.201701217,10.1021/jacs.7b12212,10.1039/c7ob02599h,10.1021/acscatal.7b02919,10.1038/NCHEM.2741,10.1002/anie.201703380,10.1002/anie.201703704,10.1039/c7sc01556a,10.1021/jacs.6b11412,10.1021/acscatal.6b01725,10.1021/jacs.6b06285,10.1021/acscatal.6b01001,10.1021/jacs.6b03384,10.1002/chem.201601112,10.1002/anie.201511663,10.1002/anie.201507494,10.1039/c6sc01457g,10.1039/c5ob02178b,10.1039/c6sc00702c,10.1002/anie.201507848,10.1002/anie.201505699,10.1021/acs.chemrev.5b00162,10.1016/j.tetlet.2015.06.071,10.1021/jacs.5b04548,10.1002/adsc.201401176,10.1021/acs.orglett.5b00766,10.1039/c5cc05209b,10.1039/c5cc03314d,10.1039/c4ob02586e,10.1021/ol503061c,10.1021/jo501406v,10.1021/ja506885s,10.1126/science.1255525,10.1002/aoc.3144,10.1021/ja500706vKelly1/24/2022
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378FALSEanie.20090699610.1002/anie.200906996https://sci-hub.wf/10.1002/anie.200906996https://doi.org/10.1002/anie.200906996NiC-H ActivationElaineTRUE22615#N/A2010Miura, M
Nickel-Catalyzed Direct C-H Arylation and Alkenylation of Heteroarenes with Organosilicon Reagents
ANGEW CHEM INT EDIT
Osaka Univ3/10/2010FALSEFALSEFALSEYCsp2_ar-Csp2_arE-NuSiH
(OMe)3-Si
HHetArylCsFIonic-F_10.1002/cctc.201000223,10.1002/chem.201001631,10.1021/ja413131m,10.1021/acscatal.6b01120,10.1002/anie.201709087,10.1002/anie.201510743,10.1016/j.tet.2013.04.096,10.1002/anie.201304492,10.1039/c5sc02942b,10.1002/anie.201300459,10.1021/ja306062c,10.1002/chem.201101091,10.1021/acs.orglett.6b02236,10.1021/ja401344e,10.1021/ja210249h10.1002/ajoc.202100792,10.1021/acs.organomet.1c00505,10.1002/adsc.202100992,10.1039/d1ob01190a,10.1002/chem.202100475,10.1002/tcr.202100113,10.1002/adsc.202001498,10.1021/acs.orglett.0c03578,10.1055/a-1335-7330,10.1016/j.tetlet.2020.152612,10.1002/ajoc.202000529,10.1007/s10562-020-03390-x,10.1021/acs.chemrev.9b00682,10.1021/acsomega.0c01150,10.1021/acs.joc.0c00560,10.1016/j.chempr.2020.04.005,10.1016/j.tetlet.2020.151807,10.1021/acs.orglett.0c00631,10.1021/acs.joc.9b03154,10.1002/adsc.201901096,10.1039/c9qo01073d,10.1002/adsc.201901078,10.1039/c9ob01883b,10.1002/anie.201911372,10.1021/acs.joc.9b02094,10.1021/acscatal.9b02841,10.1002/ajoc.201900362,10.1021/acs.orglett.9b01755,10.1016/j.tetlet.2019.05.021,10.1039/c9cc02199j,10.1021/acssuschemeng.9b00226,10.1039/c9cy00009g,10.1002/ajoc.201900069,10.1007/s11172-019-2441-3,10.1021/acs.chemrev.8b00507,10.1002/chem.201806114,10.1016/j.tetlet.2018.11.058,10.3866/PKU.WHXB201809036,10.1134/S1070428019010056,10.1002/cjoc.201800354,10.1002/slct.201802643,10.1039/c8qo00227d,10.1002/ajoc.201800002,10.1021/acs.joc.7b03055,10.1055/s-0036-1591524,10.1039/c7ob02241g,10.1039/c7qo00693d,10.1021/acs.orglett.7b03567,10.1002/anie.201709087,10.1039/c7ob01838j,10.1055/s-0036-1588487,10.1039/c7qo00318h,10.1002/ajoc.201700110,10.1002/ejoc.201700648,10.1002/chem.201605657,10.1039/c7ob00818j,10.1002/cssc.201700321,10.1021/acs.organomet.7b00129,10.1039/c7sc00156h,10.1002/hc.21360,10.1039/c6sc04371b,10.1039/c6qo00589f,10.1039/c6cc08408g,10.1021/acscatal.6b02374,10.3762/bjoc.12.272,10.1002/tcr.201600063,10.1055/s-0036-1588877,10.1021/acscatal.6b02477,10.1016/j.tetlet.2016.08.095,10.1039/c6tc03003c,10.1002/anie.201606529,10.1021/acs.orglett.6b02236,10.1002/chem.201603092,10.1007/s41061-016-0053-z,10.1002/adsc.201600590,10.1021/acscatal.6b01120,10.1021/acs.joc.6b00622,10.1021/jacs.6b04018,10.1021/acs.joc.6b00883,10.1016/j.tet.2016.02.037,10.1021/acs.organomet.6b00003,10.1002/chem.201503926,10.1002/anie.201510743,10.1016/j.jorganchem.2015.12.009,10.1039/c6ob00607h,10.1039/c6ra06915k,10.1039/c6gc02495e,10.1002/adsc.201500799,10.1021/acs.joc.5b01450,10.1021/acs.organomet.5b00733,10.1021/acs.orglett.5b02458,10.1055/s-0035-1560712,10.1002/adsc.201500515,10.1055/s-0034-1380186,10.1021/acs.orglett.5b00642,10.1021/jacs.5b00890,10.1246/cl.150024,10.6023/cjoc201410012,10.1021/acs.orglett.5b00510,10.1002/aoc.3263,10.1002/anie.201408630,10.1002/anie.201403729,10.1039/c5sc02942b,10.1039/c5dt00032g,10.1039/c5cc02254a,10.1039/c4ob02488e,10.1039/c4ra15384g,10.1038/srep07446,10.1039/c4dt01547a,10.1002/adsc.201400295,10.1021/ol502174n,10.1021/ol5018849,10.1021/ol501676q,10.1016/j.tetlet.2014.05.019,10.1246/bcsj.20140099,10.1055/s-0033-1341279,10.1021/jo5010058,10.1002/chem.201402516,10.1002/ejoc.201402091,10.1021/ol500754h,10.1016/j.jorganchem.2013.12.055,10.1021/ol500531m,10.1055/s-0033-1340320,10.1515/pac-2014-5038,10.1246/bcsj.20130166,10.1021/ja413131m,10.1021/om401204h,10.1039/c3ob42318b,10.1039/c3sc52199k,10.1039/c4gc01572j,10.3987/COM-13-S(S)13,10.1021/jo402106q,10.1002/ejoc.201301441,10.1021/ol4027073,10.1021/ja409803x,10.1002/ajoc.201300172,10.2174/15701786113109990034,10.1021/ol402494e,10.1002/anie.201304492,10.1016/j.tet.2013.04.096,10.1055/s-0033-1339193,10.1016/j.tetlet.2013.03.053,10.1021/ja401344e,10.1039/c3cc46375c,10.1039/c3cc44762f,10.1039/c3gc41027g,10.1039/c3ra41496e,10.1002/anie.201300459,10.1039/c3cc43915a,10.1002/ejoc.201200914,10.1021/ol302902e,10.1002/ejoc.201200860,10.1126/science.1225709,10.1021/jo3008594,10.1016/j.tet.2012.05.091,10.1021/ja306062c,10.1002/chem.201201450,10.1002/adsc.201200025,10.1002/asia.201101011,10.1021/ol300937z,10.1021/ol300348w,10.1021/ol300232a,10.1002/ejoc.201200050,10.1016/j.tet.2011.12.072,10.1021/ja210249h,10.1021/ol2028866,10.1021/ol203235w,10.1039/c2ob26270c,10.1039/c2cc34238c,10.1039/c2ra20366a,10.1039/c2cc18156h,10.1002/anie.201106825,10.1039/c2cs35096c,10.1039/c2gc35457h,10.1021/ja209510q,10.3762/bjoc.7.187,10.1002/chem.201102644,10.1021/jo2016168,10.1021/ol201779n,10.1021/ol2021109,10.1021/ja206850s,10.1246/cl.2011.1050,10.1246/cl.2011.1015,10.1016/j.tet.2011.06.044,10.2174/138527211796367291,10.2174/138527211796378514,10.1002/chem.201101091,10.1021/ol2009208,10.1002/ejoc.201100238,10.1021/ol2010648,10.1016/j.tet.2011.03.093,10.1021/ol200986x,10.1021/ol201160s,10.1021/jo200452x,10.1002/chem.201100037,10.1002/chem.201003039,10.1002/chem.201100136,10.1002/adsc.201000723,10.1021/jo200067y,10.1021/cr100379j,10.5059/yukigoseikyokaishi.69.252,10.1021/jo102175f,10.1021/ol1030298,10.1055/s-0030-1259332,10.1021/jo1018969,10.1002/anie.201007060,10.1039/c1cc13086b,10.1039/c0cs00125b,10.1039/c1ob05395g,10.1039/c1ob06387a,10.1021/ja109383e,10.1002/cctc.201000223,10.1021/ol101777x,10.1002/adsc.201000397,10.1021/jo100926a,10.1021/ol101450u,10.1021/ol101147b,10.1002/anie.201005082,10.1002/chem.201001631,10.1002/asia.20100052212/15/20212010FALSEFALSEFALSEFALSE49122202
359
135FALSEol403181510.1021/ol4031815https://sci-hub.wf/10.1021/ol4031815https://doi.org/10.1021/ol4031815NiC-O ActivationGerryTRUE7013182013Martin, R
Enantioselective, Nickel-Catalyzed Suzuki Cross-Coupling of Quinolinium Ions
ORGANIC LETTERS
Quinolinium ions are engaged in an asymmetric, Ni-catalyzed Suzuki cross-coupling to yield 2-aryl- and 2-heteroaryl-1,2-dihydroquinolines. Key to the development of this method is the use of a Ni(II) precatalyst that activates without the need for strong reductants or high temperatures. The Ni-iminium activation mode is demonstrated as an exceptionally mild pathway to generate enantioenriched products from racemic starting materials.
Inst Chem Res Catalonia ICIQ
12/20/2013yCsp2-Csp3E-NuOMg
O(Ring-Opening)
MgXVinylAlkylNo baseNo BaseWeak1_xxx10.1002/chem.201603436,10.1039/c4cc08187k,10.1021/acs.orglett.5b02200,10.1002/anie.201510497,10.1021/ol502583h,10.1021/acscatal.7b01058,10.1246/cl.150936,10.1021/ja5029793,10.1021/jacs.8b02134,10.1002/anie.201412051,10.1055/s-0036-1590863,10.1021/ja5076426,10.1021/ol503707m10.1021/jacs.1c10368,10.1002/adsc.202100585,10.1002/hlca.202100110,10.1039/c9cs00571d,10.1039/d1sc02210e,10.1021/jacs.1c03038,10.1039/d0cc05271j,10.1021/acs.orglett.0c02236,10.2174/1385272824666200221114707,10.1021/acs.jmedchem.9b00864,10.1021/acs.orglett.9b03170,10.3390/inorganics7100121,10.1021/acs.orglett.9b02572,10.1246/cl.190393,10.1002/cjoc.201800554,10.1021/acs.orglett.9b00946,10.1021/jacs.8b12063,10.1039/c8cc08504h,10.1002/anie.201809003,10.1002/anie.201806237,10.1039/c8cc02325e,10.1021/acs.organomet.7b00894,10.1021/acs.orglett.8b00313,10.1021/jacs.8b02134,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.1055/s-0036-1590863,10.1055/s-0036-1590962,10.1002/anie.201707309,10.1021/acs.organomet.7b00632,10.1248/cpb.c17-00487,10.1021/acscatal.7b01058,10.1039/c7cc00078b,10.1021/acs.orglett.6b03861,10.1039/c6sc02895k,10.1021/jacs.6b10998,10.1021/jacs.6b10255,10.1002/chem.201604160,10.1246/cl.160712,10.1002/chem.201603436,10.1002/asia.201600972,10.1007/s41061-016-0043-1,10.1002/anie.201510497,10.1016/bs.adomc.2016.07.001,10.1246/cl.150936,10.1021/jacs.5b08621,10.1248/yakushi.15-00201,10.1002/chem.201502114,10.1021/acs.orglett.5b02200,10.1016/j.tet.2015.02.088,10.1021/jacs.5b03955,10.1021/acs.accounts.5b00051,10.1002/aoc.3289,10.1002/ajoc.201500048,10.1002/anie.201412051,10.1246/cl.141084,10.1021/ol503707m,10.1021/cs5014927,10.1039/c5sc01460c,10.1039/c4cc08187k,10.1021/ol502583h,10.1021/ja5076426,10.1002/chem.201404380,10.1021/ja5029793,10.1039/c4cs00206gKelly1/5/2022
360
223FALSEol403209k10.1021/ol403209khttps://sci-hub.wf/10.1021/ol403209khttps://doi.org/10.1021/ol403209kNiC-O ActivationKelly12 FebTRUE156201632014Buchwald, SL
Ni-Catalyzed Stereoselective Arylation of Inert C-O bonds at Low Temperatures
ORGANIC LETTERS
A Ni-catalyzed arylation of inert C-O bonds that operates at temperatures as low as -40 degrees C is described. Unlike other methods for C-O bond cleavage utilizing organometallic species, this protocol operates at low temperatures, thus allowing the presence of sensitive functional groups with exquisite site-selectivity and stereoselectivity.
MIT1/3/2014Csp2_ar-Nsp3E-NuOH
OSO2NMe2
HAryl
N(H)Aryl
Ionic-PO4Weak0.36_xx10.1021/jacs.8b01800,10.1002/anie.202002392,10.1021/acscatal.5b00498,10.1021/ol503061c,10.1021/acscatal.6b00865,10.1021/acscatal.8b01879,10.1002/anie.202014340,10.1021/acs.orglett.7b00556,10.1002/anie.202200352,10.1021/om500452c,10.1038/ncomms11073,10.1021/jacs.7b04973,10.1002/anie.201805611,10.1021/acscatal.1c03010,10.1021/acscatal.7b02817,10.1039/c4qo00321g,10.1021/acscatal.1c04800,10.1021/ja505823s,10.1002/chem.201605095,10.1002/anie.20141087510.1002/anie.202200352,10.1021/acscatal.1c05386,10.1021/acscatal.1c05386,10.1021/acscatal.1c04800,10.1039/d1sc04011a,10.1002/anie.202108587,10.1021/acscatal.1c03010,10.3390/molecules26165079,10.1021/acs.joc.1c00577,10.1021/acs.oprd.1c00053,10.1002/anie.202103803,10.1002/ejoc.202100194,10.1002/anie.202016310,10.1002/anie.202012877,10.1002/anie.202014340,10.1021/acscatal.0c03888,10.1021/acs.oprd.0c00435,10.1039/d0ob01874k,10.1021/acs.joc.0c01771,10.1021/acs.orglett.0c02672,10.1021/acs.organomet.0c00485,10.1002/chem.202002800,10.1039/d0nj01610a,10.1016/j.mcat.2020.110915,10.1039/d0nj01139h,10.1038/s41929-020-0473-6,10.1021/acs.oprd.0c00104,10.1007/s10562-019-03062-5,10.1246/cl.200099,10.1021/acs.organomet.0c00060,10.1039/d0ob00244e,10.1021/acsomega.9b04450,10.1007/s41061-020-0300-1,10.1002/anie.202002392,10.1021/acs.organomet.9b00672,10.1021/acs.orglett.9b03434,10.1038/s41929-019-0392-6,10.1039/c9nj04436a,10.1016/j.tet.2019.130759,10.1002/ejic.201900972,10.1021/acs.organomet.9b00543,10.1002/adsc.201900545,10.1055/s-0037-1611732,10.1016/j.synthmet.2019.04.001,10.1039/c9sc00554d,10.1002/cctc.201900318,10.1002/anie.201900095,10.1021/jacs.9b01886,10.1021/acs.orglett.9b00294,10.1002/anie.201812862,10.1039/c8nj05503c,10.1021/acs.organomet.8b00451,10.1021/acs.organomet.8b00589,10.1021/acs.organomet.8b00351,10.1021/acs.orglett.8b01758,10.1002/anie.201805611,10.1021/acscatal.8b01879,10.1021/acscatal.8b02187,10.1021/acs.joc.8b00592,10.1021/acscatal.8b00933,10.1021/acscatal.8b01005,10.1016/j.jorganchem.2018.01.019,10.1002/chem.201801241,10.1021/acscatal.8b00856,10.1002/macp.201700564,10.1016/j.jechem.2017.06.003,10.1021/jacs.8b01800,10.1055/s-0036-1591523,10.1002/adsc.201701452,10.1039/c8cc00271a,10.1055/s-0036-1591853,10.1021/acs.orglett.7b03560,10.1021/acscatal.7b03215,10.1021/acscatal.7b02817,10.1002/ajoc.201700464,10.1002/anie.201707906,10.1021/jacs.7b04973,10.1002/adsc.201700672,10.1055/s-0036-1588806,10.1055/s-0036-1590819,10.1038/s41570-017-0052,10.1039/c7ob00841d,10.1002/ejic.201700057,10.1021/acs.organomet.7b00208,10.1021/acs.orglett.7b00732,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1002/ajoc.201600535,10.1038/s41570-017-0025,10.1021/acs.organomet.6b00885,10.1039/c6sc03699f,10.1021/acscatal.6b03277,10.1021/acs.joc.6b02595,10.1021/acs.joc.6b02666,10.1039/c7ra07437a,10.1002/chem.201605095,10.1002/ejoc.201600578,10.1016/j.tet.2016.08.058,10.1002/anie.201606979,10.1021/acs.organomet.6b00650,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1021/acs.orglett.6b01758,10.1002/tcr.201500305,10.1021/jacs.6b02120,10.1126/science.aag0209,10.1002/ejoc.201600112,10.1021/acscatal.6b00865,10.1021/acs.organomet.6b00059,10.1038/ncomms11073,10.1039/c6ob01307d,10.1039/c6ob00013d,10.1021/acs.oprd.5b00314,10.1021/acs.joc.5b01292,10.1002/adsc.201500461,10.1002/anie.201505136,10.1002/ejoc.201500987,10.1002/ejoc.201500734,10.1055/s-0034-1378867,10.1002/adsc.201500301,10.1021/acscatal.5b00498,10.1021/acs.orglett.5b00766,10.1002/ejoc.201500226,10.1016/j.jfluchem.2015.01.004,10.1002/cctc.201500102,10.1021/jacs.5b00538,10.1002/adsc.201500030,10.1002/anie.201500404,10.1002/anie.201410875,10.1021/acscatal.5b00072,10.1039/c4qo00321g,10.1039/c5dt02298c,10.1039/c5cc02256h,10.1039/c5cc00905g,10.1039/c4ra12658k,10.1039/c5ra17668a,10.1016/j.tetlet.2014.11.020,10.1021/ol503061c,10.1002/anie.201407944,10.1021/om500452c,10.1016/j.tetlet.2014.09.001,10.1039/c4ob00669k,10.3762/bjoc.10.189,10.1021/ja505823s,10.1002/adsc.201400405,10.1016/j.tet.2014.04.059,10.1002/adsc.201400201,10.1021/om500156q,10.1021/ja411911s,10.1039/c4sc01257gKelly2/7/2022
361
105FALSEol501672410.1021/ol5016724https://sci-hub.wf/10.1021/ol5016724https://doi.org/10.1021/ol5016724NiC-O ActivationLongTRUE534272014Watson, MP
Development of an Air-Stable Nickel Precatalyst for the Amination of Aryl Chlorides, Sulfamates, Mesylates, and Triflates
ORGANIC LETTERS
A new air-stable nickel precatalyst for C-N cross-coupling is reported. The developed catalyst system displays a greatly improved substrate scope for C-N bond formation to include both a wide range of aryl and heteroaryl electrophiles and aryl, heteroaryl, and alkylamines. The catalyst system is also compatible with a weak base, allowing the amination of substrates containing base-sensitive functional groups.
Univ Delaware7/4/2014Csp3-Csp2_arE-NuOBOPivB(OH)2AllylArylNaOMeIonic-ORMedium0.33_x10.1002/anie.201412051,10.1021/jacs.7b04973,10.1039/c7sc05216b,10.1002/anie.20150749410.1002/ejic.202100820,10.6023/cjoc202106021,10.1039/d0cs00843e,10.1021/acscatal.1c04314,10.1021/acs.orglett.1c02054,10.1021/jacs.1c08695,10.1021/acs.orglett.1c02938,10.1021/acscatal.1c03449,10.1039/d1sc02547c,10.1021/jacs.1c02117,10.1021/acs.joc.0c02690,10.1021/acscatal.0c05484,10.1002/anie.201915454,10.1021/acs.orglett.0c01109,10.1021/acs.orglett.0c00551,10.1021/acs.orglett.9b04634,10.1021/acs.orglett.9b03633,10.1021/acs.orglett.9b02946,10.1021/acscatal.9b02636,10.1021/acsomega.9b02722,10.1021/acs.joc.9b01438,10.1039/c9dt00819e,10.1021/acs.orglett.8b04030,10.1021/acscatal.8b04677,10.6023/cjoc201809037,10.1021/acs.joc.8b01320,10.1039/c8cc07093h,10.1021/acssuschemeng.8b02614,10.1021/acs.joc.8b01763,10.1016/j.jorganchem.2018.01.019,10.1039/c7sc05216b,10.1002/ajoc.201700503,10.1055/s-0036-1590962,10.1021/jacs.7b04973,10.1021/acs.orglett.7b02063,10.1126/science.aan1568,10.1002/anie.201703380,10.1002/chem.201603832,10.1021/jacs.6b07396,10.1016/j.tetlet.2016.06.022,10.1002/anie.201507494,10.1021/acs.joc.5b02151,10.1021/acs.chemrev.5b00162,10.1016/j.tet.2015.05.068,10.1002/qua.24922,10.1016/j.tetasy.2015.03.008,10.1515/pac-2014-1108,10.1002/anie.201412051,10.1016/j.tet.2015.01.046,10.1007/978-3-319-13054-5_7,10.1021/ja508067cKelly1/6/2022
362
382FALSEanie.20130045910.1002/anie.201300459https://sci-hub.wf/10.1002/anie.201300459https://doi.org/10.1002/anie.201300459NiC-H ActivationElaineTRUE2445#N/A2013Lei, AW
Direct Functionalization of Tetrahydrofuran and 1,4-Dioxane: Nickel-Catalyzed Oxidative C(sp(3))-H Arylation
ANGEW CHEM INT EDIT
Wuhan Univ3/19/2013FALSEFALSEFALSEYCsp3-Csp2_arNu-NuBHB(OH)2HAlkylArylK3PO4Ionic-PO4Nu-M_10.1039/c4cc00716f,10.1038/ncomms9404,10.1021/acs.orglett.5b02217,10.1021/acs.orglett.6b00658,10.1021/acs.joc.5b0013510.1016/j.colsurfa.2021.128202,10.1002/ajoc.202100726,10.1021/acs.orglett.1c04048,10.1039/d1cc06323e,10.1021/acs.orglett.1c04048,10.1021/acs.joc.1c02339,10.1016/j.cclet.2021.04.016,10.1002/cjoc.202100396,10.1021/acs.joc.1c02125,10.1039/d1nj05082f,10.1039/d1gc03482k,10.1021/acs.orglett.1c03223,10.1021/acs.orglett.1c03008,10.1002/adsc.202100853,10.1055/a-1631-1606,10.1021/acs.joc.1c00841,10.1039/d1nj02677a,10.1002/ejoc.202100501,10.1021/acs.orglett.1c00948,10.1021/acs.joc.0c03044,10.1070/RCR4959,10.1021/acs.joc.0c02238,10.1055/s-0040-1707183,10.1039/d0nj04187d,10.1016/j.tet.2020.131621,10.1039/d0ob01864c,10.1002/chem.202001259,10.1039/d0sc00031k,10.3390/microorganisms8081190,10.1002/anie.202004441,10.1140/epjd/e2020-100651-3,10.1021/acs.organomet.0c00021,10.1021/acs.joc.9b03294,10.1055/s-0037-1610743,10.1002/ajoc.202000007,10.1002/adsc.201901158,10.1021/acs.orglett.9b04306,10.1039/c9ob01559k,10.1039/c9ob02565k,10.1039/c9ob02203a,10.1002/ajoc.201900567,10.1021/acs.orglett.9b02295,10.1002/tcr.201800093,10.1055/s-0037-1611822,10.1002/ejoc.201900872,10.1016/j.tetlet.2019.07.013,10.1002/adsc.201900666,10.1002/slct.201901837,10.1039/c8sc05631e,10.1039/c9qo00066f,10.1021/acs.joc.9b00407,10.1039/c9qo00108e,10.1021/acs.orglett.9b00128,10.1021/acs.joc.9b00318,10.1021/acs.joc.8b03245,10.1016/j.tetlet.2019.02.021,10.1002/cctc.201801858,10.1021/acs.chemrev.8b00507,10.1016/j.tetlet.2019.01.039,10.1021/acs.orglett.8b03689,10.1021/acsomega.8b03353,10.1016/j.tetlet.2018.11.025,10.1039/c8cc08274j,10.1039/c8ob01429a,10.1021/acs.joc.8b02277,10.1039/c8qo00979a,10.1016/j.tet.2018.09.032,10.1039/c8cc06111d,10.1039/c8qo00731d,10.1021/jacs.8b07405,10.1021/acs.organomet.8b00476,10.1002/asia.201800534,10.1002/anie.201709766,10.1021/acs.joc.8b00575,10.1002/cjoc.201800106,10.6023/A18030083,10.1021/acs.orglett.8b01382,10.1039/c7qo01052d,10.1021/acs.orglett.7b03955,10.1039/c7cc08512e,10.1002/asia.201701655,10.1007/s11426-017-9142-1,10.1002/adsc.201700953,10.1016/j.chempr.2017.10.001,10.1039/c8ra01377b,10.1021/acs.orglett.7b03297,10.1039/c7cc07235j,10.1039/c7cc07089f,10.1002/anie.201707531,10.1021/acs.joc.7b01841,10.1002/chem.201702497,10.1002/adsc.201700654,10.1039/c7sc01045a,10.1055/s-0036-1588728,10.1002/chem.201701664,10.1021/acsomega.7b00386,10.1039/c7cy00535k,10.1021/jacs.7b03781,10.1002/cssc.201700321,10.1039/c6gc03323g,10.1021/acscatal.7b00094,10.1038/srep43579,10.1002/cjoc.201600538,10.1021/acs.inorgchem.6b01474,10.1002/adsc.201600467,10.1016/j.molcata.2016.11.009,10.1016/j.tet.2016.04.052,10.1021/jacs.6b04789,10.1021/jacs.6b08397,10.1002/ajoc.201600219,10.1007/s41061-016-0053-z,10.1021/acs.orglett.6b01493,10.1002/ejoc.201600423,10.1126/science.aaf6635,10.1055/s-0035-1561393,10.1021/jacs.6b02405,10.1021/acs.orglett.6b00658,10.1002/bkcs.10706,10.1021/acs.orglett.6b00304,10.1002/anie.201511002,10.1002/anie.201511321,10.1021/jacs.6b00250,10.1016/j.tetlet.2015.12.092,10.1039/c6ob02103d,10.1016/bs.aihch.2015.10.003,10.1039/c6ra12657j,10.1039/c5ob02478a,10.1039/c5ra27899f,10.1039/c5cc08952b,10.1039/c5cc07175e,10.1016/j.jorganchem.2015.10.010,10.1039/c6cc07626b,10.1002/ejoc.201501300,10.1016/bs.aihch.2016.04.005,10.6023/A15060407,10.1055/s-0035-1560661,10.1021/acs.orglett.5b02749,10.1021/acs.joc.5b01990,10.1038/srep15934,10.1055/s-0035-1560180,10.1021/acs.organomet.5b00733,10.1021/acs.orglett.5b02217,10.1021/jacs.5b06740,10.1021/acs.orglett.5b02116,10.1016/j.jorganchem.2015.03.023,10.1038/ncomms9404,10.1021/jacs.5b05665,10.3390/molecules200713336,10.1002/chem.201500560,10.1002/anie.201412026,10.1016/j.tet.2015.02.035,10.1021/jo502903d,10.1055/s-0034-1380125,10.1055/s-0034-1380320,10.1021/acs.joc.5b00135,10.1021/acs.orglett.5b00088,10.1021/acs.joc.5b00025,10.1021/acs.orglett.5b00104,10.1016/j.molstruc.2014.10.068,10.1002/ejoc.201403274,10.1002/anie.201410322,10.1021/ja510635k,10.1039/c5ob01268f,10.1039/c4qo00293h,10.1039/c4qo00314d,10.1039/c5qo00208g,10.1039/c5cy00876j,10.1039/c5cc05005g,10.1039/c5ra11530b,10.1039/c5dt01516b,10.1039/c5cc01287b,10.1039/c4nj02416h,10.3998/ark.5550190.p008.915,10.1039/c4ob02564d,10.1039/c4ob02621g,10.1039/c4ob02250e,10.1039/c4cc07654k,10.1039/c4cc08797f,10.1039/c4cc10015h,10.1002/chem.201404463,10.1038/srep07446,10.1021/om500767p,10.1002/anie.201407083,10.1021/ar5002044,10.1002/asia.201403052,10.1021/ol503004a,10.1002/chem.201404440,10.1002/adsc.201400646,10.1055/s-0034-1378555,10.1016/j.tetlet.2014.09.042,10.1021/ol502524d,10.1002/adsc.201400295,10.1021/ol502314p,10.1016/j.tet.2014.07.022,10.1039/c4cc04282d,10.1039/c4cc03149k,10.1007/s11426-014-5118-7,10.1055/s-0033-1341279,10.1021/jo500905m,10.1021/ol501485f,10.1021/ol5011449,10.1021/ol5011906,10.1021/ja503520t,10.1021/jo500192h,10.1021/ol500277u,10.1021/ol5007778,10.1021/ol5004115,10.6023/cjoc201311024,10.1515/pac-2014-5034,10.1002/cctc.201301058,10.1007/s10562-013-1170-8,10.1021/jo4027885,10.1021/ja4118472,10.1039/c4qo00006d,10.1039/c4cc05661b,10.1039/c4ra06233g,10.1080/00397911.2014.888081,10.1039/c4cc03348e,10.1039/c4cc00743c,10.1039/c4ob00002a,10.1039/c4cc00716f,10.1039/c4cc00867g,10.1039/c3dt52412d,10.1039/c3cy00503h,10.1039/c4cc05758a,10.1039/c4cc06003b,10.1039/c4ra10939b,10.1002/anie.201307865,10.1039/c3ob41851k,10.1021/ol402869h,10.1016/j.tetlet.2013.09.082,10.1039/c3ob41392f,10.1021/ol402281f,10.1021/ol4022113,10.1039/c3cc46375c,10.1039/c3cc45499a12/15/20212013FALSEFALSEFALSEFALSE52164453
363
383FALSEja413131m10.1021/ja413131mhttps://sci-hub.wf/10.1021/ja413131mhttps://doi.org/10.1021/ja413131mNiC-H ActivationElaineTRUE10120#N/A2014Ge, HB
Nickel-Catalyzed Site-Selective Alkylation of Unactivated C(sp(3))-H Bonds
J AM CHEM SOC
The direct alkylation of unactivated sp(3) C-H bonds of aliphatic amides was achieved via nickel catalysis with the assist of a bidentate directing group. The reaction favors the C-H bonds of methyl groups over the methylene C-H bonds and tolerates various functional groups. Moreover, this reaction shows a predominant preference for sp(3) C-H bonds of methyl groups via a five-membered ring intermediate over the sp(2) C-H bonds of arenes in the cyclometalation step.
Indiana Univ Purdue Univ
2/5/2014TRUEFALSEFALSEyCsp3-Csp3E-NuXHIHAlkylAlkylCs2CO3Ionic-CO3_corrected 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Nickel-Catalyzed Reaction of Arylzinc Reagents with N-Aromatic Heterocycles: A Straightforward Approach to C-H Bond Arylation of Electron-Deficient Heteroaromatic Compounds
J AM CHEM SOC
The reaction of electron-deficient N-heteroaromatic compounds, such as pyridines and quinolines, with arylzinc reagents in the presence of a catalytic amount of a nickel complex affords the arylated products. The reaction is likely to proceed through a format nucleophilic 1,2-addition, thus exhibiting a reactivity complementary to conventional direct arylation through electrophilic substitution.
Osaka Univ9/2/2009TRUEFALSETRUEyCsp2_ar-Csp2_arE-NuZnHZn(Ph)HHetArylNo baseNo 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174FALSEol501707z10.1021/ol501707zhttps://sci-hub.wf/10.1021/ol501707zhttps://doi.org/10.1021/ol501707zNiC-O ActivationGerryTRUE926272014Zeng, XM
Enantiospecific, Nickel-Catalyzed Cross-Couplings of Allylic Pivalates and Arylboroxines
ORGANIC LETTERS
We have developed an enantiospecific, nickel-catalyzed cross-coupling of unsymmetric 1,3-disubstituted allylic pivalates with arylboroxines. The success of this reaction relies on the use of BnPPh2 as a supporting ligand for the nickel(0) catalyst and NaOMe as a base. This method shows excellent functional group tolerance and broad scope in both the allylic pivalate and arylboroxine, enabling the preparation of 1,3-diaryl allylic products in high yields with excellent levels of regioselectivity and stereochemical fidelity.
Xi An Jiao Tong Univ
8/1/2014Csp3-Csp2_arE-NuOH
OP(O)(OEt)2
HAllylArylNa2CO3Ionic-CO3Strong0.04_10.1021/acs.orglett.6b02236,10.1039/d1cc02983e,10.1021/acs.joc.5b00669,10.1039/c6qo00149a,10.1039/c5cc01436k,10.1246/bcsj.2014038710.1002/ejoc.202100717,10.1021/acs.orglett.1c01832,10.1039/d1cc02983e,10.1002/tcr.202100117,10.1055/a-1477-7059,10.1016/j.chempr.2020.10.020,10.1021/acscatal.0c01436,10.1055/s-0037-1610756,10.1080/00397911.2020.1761392,10.1002/anie.202003632,10.1002/cjoc.201900468,10.1021/acs.chemrev.9b00495,10.1039/c9nj02191d,10.1039/c8qo01425f,10.1039/c8sc05063e,10.1039/c8qo01274a,10.1021/acs.chemrev.8b00507,10.1002/cctc.201801625,10.1039/c8cy01860j,10.1002/anie.201712520,10.1039/c8ob01481g,10.1039/c8sc01741g,10.1039/c7sc04604a,10.1021/acs.orglett.7b03440,10.1002/ajoc.201700515,10.1039/c8ra01377b,10.1021/acs.orglett.7b02983,10.1021/jacs.7b03548,10.1002/chem.201605657,10.1039/c7sc01204g,10.1002/cssc.201700452,10.1016/j.tet.2017.02.021,10.1021/acscatal.7b00159,10.1021/acs.orglett.6b03856,10.1039/c6qo00479b,10.1039/c6ob02224c,10.1002/open.201600096,10.1021/acscatal.6b02477,10.1021/acs.orglett.6b02229,10.1021/acs.orglett.6b02236,10.1021/acs.orglett.6b02146,10.1039/c6cc05330k,10.1021/acs.inorgchem.6b01162,10.1021/acscatal.6b01816,10.1007/s41061-016-0053-z,10.1021/acs.orglett.6b01566,10.1021/acs.orglett.6b01288,10.1016/j.tetlet.2016.04.089,10.3762/bjoc.12.108,10.1002/adsc.201600080,10.1021/acscatal.6b00993,10.1021/jacs.6b02405,10.1021/acs.orglett.6b00846,10.1002/chem.201600229,10.1002/ejoc.201501551,10.1002/adsc.201500884,10.1007/3418_2015_117,10.1039/c6qo00178e,10.1039/c6qo00149a,10.1039/c6ra07450b,10.1039/c6cc02412b,10.1039/c6ob00164e,10.1039/c6qo00011h,10.1021/acs.orglett.5b03142,10.1016/j.jorganchem.2015.03.023,10.1002/ajoc.201500105,10.1002/anie.201503704,10.1021/acs.orglett.5b01701,10.1002/chem.201500639,10.1021/acs.joc.5b00669,10.1021/acs.orglett.5b00990,10.1021/acs.joc.5b00580,10.1021/jacs.5b01671,10.1246/cl.150024,10.1246/bcsj.20140387,10.1039/c5dt00032g,10.1039/c5cc01970b,10.1039/c5cc01436k,10.1039/c5cc01163a,10.1007/s10562-014-1449-4,10.1039/c4cc09899d,10.1039/c4cc10446c,10.1021/ja511011m,10.1021/jo501697n,10.1021/ol503229cKelly12/28/2021
366
191FALSEol502583h10.1021/ol502583hhttps://sci-hub.wf/10.1021/ol502583hhttps://doi.org/10.1021/ol502583hNiC-O ActivationLongTRUE10416892014Chatani, N
Nickel-Catalyzed C-H Coupling with Allyl Phosphates: A Site-Selective Synthetic Route to Linear Allylarenes
ORGANIC LETTERS
It is reported that a nickel/phosphine catalyst allows the C-H allylation to occur effectively with the allyl site selectivity predominantly governed by steric effects. This reaction provides a facile and predictable route for the selective preparation of linear allylarenes from readily available benzamides and allyl phosphates.
Osaka Univ11/7/2014FALSEFALSECsp3-ring(s)-Csp2_arE-NuOBOMeB(nep)BenzylArylCsFIonic-FStrong-0.28_xAdded by Long10.1002/anie.201510497,10.1002/chem.201603436,10.1021/jacs.0c12462,10.1021/jacs.7b04973,10.1246/cl.150936,10.1038/NCHEM.2741,10.1002/ejic.201900692,10.1021/acs.orglett.5b02200,10.1021/acs.orglett.5b03151,10.1021/acs.joc.6b01627,10.1021/jacs.7b04279,10.1002/anie.201607646,10.1021/acscatal.8b03436,10.1021/ol503707m,10.1021/jacs.6b03253,10.1021/acscatal.6b0080110.1021/acscatal.1c02790,10.1021/jacs.1c05281,10.1039/d1qo00549a,10.1039/d1qo00656h,10.1021/jacs.1c03038,10.1055/a-1467-2494,10.1021/acs.orglett.0c04316,10.1021/jacs.0c12462,10.1055/a-1349-3543,10.1021/acs.orglett.0c03507,10.1002/chem.202004132,10.1021/acs.chemrev.0c00088,10.1002/asia.202000763,10.1002/cjoc.201900506,10.1021/jacs.0c02839,10.1021/acs.joc.9b03433,10.1016/j.tetlet.2020.151729,10.1002/anie.202001211,10.1055/s-0039-1690718,10.1002/jccs.201900450,10.1039/c9cc07558e,10.1021/acs.orglett.9b03475,10.1021/acs.orglett.9b03170,10.1021/acs.orglett.9b02910,10.3390/molecules24193523,10.1002/adsc.201900745,10.1002/ejic.201900692,10.1021/acs.orglett.9b01669,10.1016/j.tetlet.2019.04.004,10.1002/ejoc.201801888,10.1021/acs.organomet.8b00720,10.1007/3418_2018_19,10.1021/acs.oprd.8b00325,10.1021/acscatal.8b03436,10.1002/adsc.201801135,10.1021/acs.joc.8b02104,10.1021/acs.orglett.8b01696,10.1016/j.jorganchem.2018.01.019,10.1021/jacs.8b02547,10.1038/s41467-018-03928-z,10.1021/acs.orglett.8b00674,10.1021/acs.orglett.8b00080,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.1039/c8ra07841f,10.1039/c8ra06780e,10.1055/s-0036-1589093,10.1055/s-0036-1588568,10.1055/s-0036-1590985,10.1021/acsomega.7b01450,10.1021/jacs.7b04973,10.1021/jacs.7b04279,10.1038/NCHEM.2741,10.1039/c7ob00911a,10.1021/jacs.7b02742,10.1039/c7cc00255f,10.1246/bcsj.20160391,10.1002/anie.201610409,10.1016/j.cclet.2016.09.006,10.1021/jacs.6b10998,10.1021/acscatal.6b02964,10.1002/anie.201607646,10.1246/cl.160712,10.1021/jacs.6b09533,10.1002/chem.201603436,10.1021/acs.joc.6b01627,10.1016/j.tetlet.2016.07.089,10.1007/s41061-016-0043-1,10.1002/adsc.201600336,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1002/ejoc.201600385,10.1021/jacs.6b03253,10.1002/anie.201510497,10.3762/bjoc.12.65,10.1002/adsc.201500358,10.1016/bs.adomc.2016.07.001,10.1039/c6gc00367b,10.1039/c5qo00395d,10.1021/acs.joc.5b02557,10.1021/acs.orglett.5b03151,10.1246/cl.150936,10.1021/jacs.5b08621,10.1021/jacs.5b10119,10.3762/bjoc.11.235,10.1002/chem.201502114,10.1021/acs.orglett.5b02200,10.1021/acscatal.5b00909,10.1021/acs.accounts.5b00223,10.1016/j.tet.2015.05.068,10.1021/acs.orglett.5b01229,10.1016/j.tet.2015.02.088,10.1021/jacs.5b03955,10.1021/acs.accounts.5b00051,10.1246/cl.141084,10.1021/ol503707m,10.1039/c5qo00039d,10.1039/c5sc00305a,10.1039/c4ra16452kKelly11/9/2021
367
387TRUEja306062c10.1021/ja306062chttps://sci-hub.wf/10.1021/ja306062chttps://doi.org/10.1021/ja306062cNiC-H ActivationGerryTRUE13426492012Yamaguchi, J
DeCarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A
J AM CHEM SOC
A nickel-catalyzed deCarbonylative C-H biaryl coupling of azoles and aryl esters is described. The newly developed catalytic system does not require the use of expensive metal catalysts or silver- or copper-based stoichiometric oxidants. We have successfully applied this new C-H arylation reaction to a convergent formal synthesis of muscoride A.
Nagoya 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368
388FALSEol900158710.1021/ol9001587https://sci-hub.wf/10.1021/ol9001587https://doi.org/10.1021/ol9001587NiC-H ActivationShihongTRUE26015802009Itami, K
Nickel-Catalyzed Biaryl Coupling of Heteroarenes and Aryl Halides/TriflatesORG LETT
Ni-based catalytic systems for the arylation of heteroarenes with aryl halides and triflates have been established. Ni(OAc)(2)/bipy is a general catalyst for aryl bromides/iodides, and Ni(OAC)(2)/dppf is effective for aryl chlorides/triflates. Thiazole, benzothiazole, oxazole, benzoxazole, and benzimidazole are applicable as heteroarene coupling partners. A rapid synthesis of febuxostat, a drug for gout and hyperuricemia, is also demonstrated.
Nagoya 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369
389FALSEnchem.238810.1038/nchem.2388https://sci-hub.wf/10.1038/nchem.2388https://doi.org/10.1038/nchem.2388NiC-N ActivationGerryTRUE2764542016Garg, NK
Nickel-catalysed Suzuki-Miyaura coupling of amidesNAT CHEM
The Suzuki-Miyaura coupling has become one of the most important and prevalent methods for the construction of C-C bonds. Although palladium catalysis has historically dominated the field, the use of nickel catalysis has become increasingly widespread because of its unique ability to cleave carbon-heteroatom bonds that are unreactive towards other transition metals. We report the first nickel-catalysed Suzuki-Miyaura coupling of amides, which proceeds by an uncommon cleavage of the amide C-N bond after N-tert-butoxyCarbonyl activation. The methodology is mild, functional-group tolerant and can be strategically employed in sequential transition-metal-catalysed cross-coupling sequences to unite heterocyclic fragments. These studies demonstrate that amides, despite classically considered inert substrates, can be harnessed as synthons for use in reactions that form C-C bonds through cleavage of the C-N bond using non-precious metal catalysis.
Univ Calif Los Angeles
1/1/2016TRUETRUEFALSECsp2-Csp2_arE-NuNB
N(Bn)Boc
Bpin
Carbonyl
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370
102FALSEol502682q10.1021/ol502682qhttps://sci-hub.wf/10.1021/ol502682qhttps://doi.org/10.1021/ol502682qNiC-O ActivationLongTRUE631082014Lin, KH
1,3-Dicyclohexylimidazol-2-ylidene as a Superior Ligand for the Nickel-Catalyzed Cross-Couplings of Aryl and Benzyl Methyl Ethers with Organoboron Reagents
ORGANIC LETTERS
A new catalytic system has been developed involving the use of Ni(cod)2 in conjunction with 1,3-dicyclohexylimidazol-2-ylidene for the cross-coupling of aryl and benzyl methyl ethers with organoboron reagents. This method not only allows for the use of readily available methyl ethers as halide surrogates but also provides a functional group tolerant method for the late-stage derivatization of complex molecules.
Shanghai Univ11/7/2014yCsp3-Csp2E-EOXOTsClAlkyl
Carbonyl
#N/ANo BaseWeak0.36_10.1002/chem.201601320,10.1039/c7cc06106d,10.1039/c9sc03347e,10.1021/jacs.7b02389,10.1021/jacs.0c01330,10.1021/acs.orglett.9b01164,10.1021/acs.joc.5b00135,10.1021/acs.orglett.9b00174,10.1039/c5cc03113c,10.1039/c7cc01932g10.1021/acs.joc.1c02188,10.6023/cjoc202106021,10.1021/acs.orglett.1c02458,10.1039/c9cs00571d,10.1039/d1qo00549a,10.1126/science.abh2623,10.1055/s-0040-1706013,10.1055/s-0040-1707342,10.1021/acs.orglett.0c03342,10.1055/s-0040-1705987,10.6023/cjoc202006075,10.1021/acsomega.0c04181,10.1021/acs.accounts.0c00291,10.1021/jacs.0c04812,10.1002/chem.202001180,10.1021/jacs.0c02673,10.1021/jacs.0c02805,10.1021/jacs.0c01330,10.1021/jacs.9b07857,10.1039/c9sc03347e,10.1002/chem.201903668,10.1016/j.tetlet.2019.150991,10.1021/acs.orglett.9b01987,10.6023/cjoc201902011,10.1021/acs.orglett.9b01164,10.1021/acs.orglett.9b00174,10.1002/chem.201803642,10.6023/cjoc201806038,10.1021/acs.orglett.9b00100,10.1021/jacs.8b12025,10.1016/bs.aihch.2017.10.001,10.1039/c7cc06106d,10.6023/cjoc201703042,10.1039/c7cc01932g,10.1021/jacs.7b02389,10.1016/j.jscs.2016.10.001,10.1021/jacs.6b09533,10.1007/s41061-016-0042-2,10.1002/chem.201601320,10.1021/jacs.6b01533,10.1039/c6ob01281g,10.1055/s-0035-1560531,10.1002/chem.201501543,10.6023/cjoc201503007,10.1021/acs.orglett.5b01612,10.1002/anie.201502882,10.1021/acs.joc.5b00135,10.1039/c5nj01597a,10.1039/c5cc03113c,10.1039/c5qo00224aKelly2/17/2022
371
76FALSEol503061c10.1021/ol503061chttps://sci-hub.wf/10.1021/ol503061chttps://doi.org/10.1021/ol503061cNiC-O ActivationGerryTRUE4451062014Percec, V
Nickel-Catalyzed Reductive Methylation of Alkyl Halides and Acid Chlorides with Methyl p-Tosylate
ORGANIC LETTERS
Methylation of unactivated alkyl halides and acid chlorides under Ni-catalyzed reductive coupling conditions led to efficient formation of methylated alkanes and ketones using methyl p-methyl tosylate as the methylation reagent. Moderate to excellent coupling yields as well as excellent functional group tolerance were observed under the present mild and easy-to-operate reaction conditions.
Univ Penn12/19/2014not reactant scopeCsp2_ar-Csp2_arE-NuOB
OSO2NMe2
B(nep)ArylArylK3PO4 · 3H2OIonic-PO4Weak0.36_10.1021/jacs.6b11412,10.1021/acscatal.9b00744,10.1021/jacs.1c08502,10.1002/anie.201805611,10.1038/NCHEM.238810.1002/ejic.202101006,10.1021/jacs.1c08502,10.1002/ijch.202100057,10.1055/a-1548-8362,10.1021/acs.joc.1c00577,10.1021/acscatal.0c03334,10.1016/j.intermet.2020.106839,10.1021/acs.biomac.0c00507,10.1039/d0ob00244e,10.1002/ijch.202000004,10.2174/1570193X16666190617160339,10.1021/acs.orglett.9b01355,10.1021/acscatal.9b00744,10.1039/c8nj05503c,10.1016/j.mcat.2018.09.022,10.1016/j.tet.2018.10.025,10.1021/acs.organomet.8b00589,10.3390/molecules23102435,10.1021/acs.organomet.8b00351,10.1002/anie.201805611,10.1021/jacs.8b04479,10.1039/c8dt01288a,10.1002/chem.201801241,10.1021/acscatal.8b00230,10.1039/c8cc00271a,10.1021/acs.organomet.7b00642,10.1002/adsc.201601105,10.1038/s41570-017-0025,10.1021/acs.joc.6b02666,10.1021/jacs.6b11412,10.1021/acs.joc.6b02093,10.1021/acs.orglett.6b02330,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1021/acs.orglett.6b01758,10.1021/acs.macromol.6b01006,10.1021/acs.organomet.6b00059,10.1002/ejoc.201501170,10.1038/NCHEM.2388,10.1021/acs.orglett.5b00766,10.1039/c4cy01736f1/5/2022
372
185FALSEol503707m10.1021/ol503707mhttps://sci-hub.wf/10.1021/ol503707mhttps://doi.org/10.1021/ol503707mNiC-O ActivationLongTRUE9722892015Chatani, N
Air-Stable Nickel Precatalysts for Fast and Quantitative Cross-Coupling of Aryl Sulfamates with Aryl Neopentylglycolboronates at Room Temperature
ORGANIC LETTERS
A library containing 10 air-stable (NiX)-X-II(Aryl)(PCy3)(2) sigma-complexes as precatalysts (X = Cl, Br, OTs, OMs, aryl = 1-naphthyl, 2-naphthyl; X = Cl, 1-acenaphthenyl, 1-(2-methoxynaphthyl), 9-phenanthrenyl, 9-anthracyl) was synthesized and demonstrated to quantitatively cross-couple 2-methoxyphenyl dimethylsulfamate with methyl 4-(5,5-dimethyl-1,3,2-dioxaborinane-2-yl)benzoate at 23 degrees C in dry THF in the presence of K3PO4(H2O)(3.2) in less than 60 min. Lower or higher amounts of H2O in K3PO4 and as received THF mediate the same transformation in a maximum three times longer reaction time.
Osaka Univ2/6/2015FALSETRUECsp2_ar-Csp1E-NuOMgOMeMgXArylAlkyneNo baseNo BaseStrong-0.28_xAdded by Long10.1021/acscatal.7b01058,10.1021/jacs.7b04279,10.1002/anie.201510497,10.1002/chem.201603436,10.1021/acs.orglett.6b00819,10.1021/acscatal.6b01120,10.1021/jacs.7b02326,10.1021/acs.orglett.5b03151,10.1021/acs.orglett.5b02200,10.1002/ejic.201900692,10.1021/acs.organomet.5b00874,10.1002/anie.201806790,10.1021/acscatal.9b00744,10.1021/jacs.7b04973,10.1021/acs.joc.6b01627,10.1021/acscatal.6b00801,10.1021/jacs.8b02134,10.1246/cl.150936,10.1021/acs.orglett.6b02656,10.1021/jacs.6b03253,10.1021/acscatal.8b03436,10.1002/anie.20160764610.1002/adsc.202100992,10.1039/d1qo00549a,10.1021/acscatal.1c01077,10.1021/jacs.1c03038,10.1055/a-1467-2494,10.1021/acs.inorgchem.0c03664,10.1007/s41061-020-00316-4,10.1039/d0qo00785d,10.1021/acs.orglett.0c03507,10.1021/acs.organomet.0c00573,10.1021/acs.chemrev.0c00088,10.1002/asia.202000763,10.1002/cctc.202000876,10.1039/d0sc01585g,10.1002/cjoc.201900506,10.1246/cl.200083,10.1039/c9cc08663c,10.1002/jccs.201900450,10.1002/open.201900246,10.1021/acs.orglett.9b02504,10.1002/adsc.201900745,10.1002/ejic.201900692,10.1002/anie.201902315,10.1021/acscatal.9b00744,10.1021/acs.organomet.8b00720,10.1007/3418_2018_19,10.1070/RCR4855,10.1021/acscatal.8b03436,10.1021/acs.joc.8b02104,10.1002/anie.201806790,10.1021/acs.orglett.8b01696,10.1055/s-0036-1591979,10.1016/j.jorganchem.2018.01.019,10.1021/acscatal.8b01224,10.1038/s41467-018-03928-z,10.1021/acs.orglett.8b00313,10.1021/acs.orglett.8b00674,10.1021/jacs.8b02134,10.1002/cjoc.201700664,10.1039/c7cc08709h,10.1039/c7cy01205e,10.1055/s-0036-1589093,10.1055/s-0036-1588568,10.1039/c7qo00327g,10.1021/jacs.7b04973,10.1248/cpb.c17-00487,10.1021/jacs.7b04279,10.1021/acscatal.7b01058,10.1021/jacs.7b02326,10.1021/acs.orglett.6b03861,10.1246/bcsj.20160391,10.1002/anie.201610409,10.1021/acscatal.6b02964,10.1002/anie.201607646,10.1021/acs.orglett.6b02656,10.1002/ajoc.201600411,10.1246/cl.160712,10.1002/chem.201603436,10.1021/acs.orglett.6b02549,10.1021/acs.joc.6b01627,10.1002/asia.201600972,10.1002/asia.201600943,10.1007/s41061-016-0043-1,10.1021/acscatal.6b00801,10.1021/acscatal.6b01120,10.1021/acs.orglett.6b00819,10.1021/jacs.6b03253,10.1002/anie.201510497,10.3762/bjoc.12.65,10.1016/bs.adomc.2016.07.001,10.1039/c6ob01807f,10.1039/c5qo00395d,10.1021/acs.joc.5b02557,10.1021/acs.organomet.5b00874,10.1021/acs.orglett.5b03151,10.1246/cl.150936,10.1021/jacs.5b08621,10.1021/jacs.5b10119,10.3762/bjoc.11.235,10.1021/jacs.5b07677,10.1002/chem.201502114,10.1021/acs.orglett.5b02200,10.1002/anie.201504066,10.1016/j.tet.2015.02.088,10.1021/acs.accounts.5b00051,10.1039/c5qo00039d,10.1039/c5cc04390e,10.1039/c5sc00305a,10.1039/c5cc01378jKelly11/9/2021
373
393FALSEja034908b10.1021/ja034908bhttps://sci-hub.wf/10.1021/ja034908bhttps://doi.org/10.1021/ja034908bNiC-N ActivationKellyTRUE19430#N/A2003
MacMillan, DWC
The first Suzuki cross-couplings of aryltrimethylammonium salts
J AM CHEM SOC
CALTECH5/21/2003FALSEFALSEFALSECsp2_ar-Csp2_arE-NuNB
NMe3+OTf-
B(OH)2ArylArylCsFIonic-FE-H_xx10.1021/ja3089422,10.1016/j.tet.2017.06.004,10.1038/nature14615,10.1021/ja505823s,10.1038/ncomms12937,10.1021/acs.orglett.9b00242,10.1021/jacs.6b11412,10.1039/c3ob41989d,10.1021/acscatal.7b01058,10.1002/anie.201100683,10.1039/c6ob01299j,10.1038/NCHEM.2388,10.1002/chem.201603436,10.1002/ejoc.201001519,10.1002/anie.200900329,10.1021/jo4005537,10.1021/ol048490d,10.1021/jacs.7b02389,10.1039/c2dt30886j,10.1002/anie.201102092,10.1039/c4qo00321g,10.1021/jo300209d,10.1002/ajoc.201700569,10.1021/om500452c,10.1021/ol9029534,10.1002/anie.201511197,10.1021/ol901978e,10.1021/jacs.9b00111,10.1021/jacs.9b05224,10.1021/jacs.8b0877910.1021/acs.orglett.1c03590,10.1021/acs.orglett.1c03048,10.3390/molecules26195947,10.1039/d1ob01690c,10.1039/d1ob01468d,10.1021/acs.joc.1c01339,10.1039/d1gc01907d,10.1039/c9cs00571d,10.1039/d1qo00759a,10.1021/jacs.1c04427,10.1021/acs.orglett.1c01503,10.1039/d1cc01734a,10.1039/d1sc00757b,10.1039/d1cy00312g,10.1039/d0nj06271e,10.1016/j.mcat.2021.111500,10.1021/acs.joc.0c02992,10.1021/acscatal.0c05484,10.1021/acs.orglett.0c03660,10.1021/acs.joc.0c01928,10.1055/a-1326-6973,10.1021/acscatal.0c03341,10.1002/adsc.202000821,10.1021/acscatal.0c03334,10.1021/acscatal.0c02990,10.1021/acscatal.0c01462,10.1021/acs.joc.0c01274,10.1039/d0sc01229g,10.1021/acs.orglett.0c01869,10.1002/anie.202006740,10.1016/j.catcom.2020.106009,10.1016/j.tetlet.2020.151975,10.1002/asia.202000476,10.1039/d0qo00173b,10.1002/cjoc.201900468,10.1039/d0ob00563k,10.1002/chem.202000412,10.1021/acs.orglett.9b04647,10.1039/c9ob02667c,10.1002/ajoc.201900759,10.1055/s-0039-1690703,10.1021/acs.organomet.9b00672,10.1039/c9ob02107h,10.1021/acs.joc.9b02554,10.1039/c9qo01033e,10.1021/acs.orglett.9b04068,10.1021/acs.orglett.9b03393,10.1016/j.jorganchem.2019.120937,10.1021/acs.orglett.9b02961,10.1016/j.isci.2019.08.021,10.1021/acs.joc.9b01877,10.1002/anie.201908336,10.1021/acs.organomet.9b00543,10.1021/acs.orglett.9b02820,10.1021/acscatal.9b02440,10.1016/j.tet.2019.07.007,10.1021/jacs.9b05224,10.1016/j.isci.2019.04.038,10.1039/c9sc01083a,10.1021/jacs.9b02312,10.1002/chem.201900886,10.1021/acscatal.9b00218,10.1021/acs.orglett.9b00499,10.1039/c8ob02992j,10.1002/chem.201803642,10.1039/c8ra10439e,10.1021/acs.orglett.9b00242,10.1021/jacs.9b00111,10.1021/acs.joc.8b02926,10.1039/c8nj05503c,10.1021/acs.joc.8b02150,10.1021/acs.joc.8b02567,10.1021/jacs.8b08792,10.1021/acscatal.8b03437,10.1039/c8cc07093h,10.1021/jacs.8b08779,10.1021/acscatal.8b02495,10.6023/cjoc201803013,10.1038/s41467-018-05637-z,10.1002/anie.201806271,10.1002/anie.201804628,10.1039/c8cc03760d,10.1021/acs.joc.8b00965,10.1021/acscatal.8b00933,10.1021/acs.orglett.8b01233,10.1039/c8ob00488a,10.1021/jacs.8b02462,10.6023/cjoc201710034,10.1038/s41467-018-03928-z,10.1021/acs.orglett.8b00545,10.1002/anie.201712618,10.1002/cjoc.201700664,10.1055/s-0036-1588548,10.1021/acs.joc.7b02588,10.1002/ajoc.201700569,10.1002/ajoc.201700550,10.1039/c7qo00731k,10.1002/asia.201701342,10.1055/s-0036-1590893,10.1039/c7gc02775c,10.1002/ijch.201700044,10.1021/jacs.7b08579,10.1039/c7cs00182g,10.1002/asia.201701132,10.1002/ajoc.201700242,10.1021/acscatal.7b02540,10.1007/s10934-017-0381-6,10.1021/jacs.7b08053,10.1039/c7sc02692g,10.1039/c7sc02181j,10.1002/anie.201704948,10.1016/j.tet.2017.06.004,10.1021/jacs.7b03159,10.1002/asia.201700313,10.1021/acs.orglett.7b01575,10.1039/c7qo00174f,10.1021/jacs.7b05273,10.1021/acscatal.7b01058,10.6023/cjoc201612014,10.1039/c6sc05705e,10.1021/jacs.7b02389,10.1039/c6cc08701a,10.1021/acscatal.6b03277,10.1021/jacs.6b11412,10.1039/c7ra10755b,10.1039/c7ra02549a,10.1016/j.tet.2016.10.018,10.1021/acscatal.6b02323,10.1002/chem.201603436,10.1021/jacs.6b08164,10.1002/slct.201600962,10.1038/ncomms12937,10.1002/adsc.201600590,10.1002/anie.201601914,10.1016/j.tetlet.2016.04.009,10.1002/anie.201600400,10.1016/j.jorganchem.2016.02.005,10.1002/anie.201600697,10.1002/anie.201511197,10.1039/c6cc06089g,10.1039/c6ob01299j,10.1039/c6cy00597g,10.1039/c6cc04531f,10.1039/c5cs00534e,10.1039/c6dt02995g,10.1021/acs.joc.5b02557,10.1038/NCHEM.2388,10.1039/c6ob01038e,10.1002/anie.201507776,10.1002/chem.201503596,10.1021/acs.chemrev.5b00386,10.1002/anie.201508161,10.1021/acs.orglett.5b02458,10.1021/acs.orglett.5b02209,10.1021/acs.orglett.5b02380,10.1038/nature14615,10.1016/j.tet.2015.05.068,10.1021/jacs.5b05086,10.1002/adsc.201500304,10.1038/ncomms8508,10.1021/cs5014927,10.1039/c5ra17740e,10.1039/c4qo00321g,10.1007/978-3-319-13054-5_7,10.1039/c5ra05131b,10.1039/c4cc08925a,10.1039/c5ra12512j,10.1021/jo502123k,10.1021/om500452c,10.1002/adsc.201400155,10.1055/s-0034-1378208,10.1021/ja505823s,10.1002/ejoc.201402475,10.1038/NCHEM.1971,10.1021/ol501180q,10.1002/ejoc.201402353,10.1002/ejoc.201400126,10.1021/ja501649a,10.1002/aoc.3126,10.1021/jo500026g,10.1002/pi.4513,10.1039/c3ob41989d,10.1016/j.molcata.2013.10.014,10.1039/c3py01551c,10.1039/c4ra11520a,10.1021/om401000s,10.1021/ja410760f,10.1016/j.tet.2013.09.039,10.1021/jo401915t,10.1002/ajoc.201300172,10.1016/j.jorganchem.2013.06.001,10.1021/j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374
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Nickel-Catalyzed Alkynylation of Anisoles via C-O Bond Cleavage
ORGANIC LETTERS
A new cross-coupling reaction has been developed for the introduction of an alkyne moiety to an anisole derivative through C-O bond activation using an NHC ligand. This method has been used for direct alkynylation of a broad range of anisole derivatives and provided rapid access to compounds with potential applications in biological and materials science.
10/25/2007Csp3-Osp2E-NuOHOAcHAlkylORIonic-HMedium0.31_10.1002/chem.201502329,10.1021/ol403136410.1039/d1cy02085d,10.1002/ejic.202100820,10.1021/acs.joc.1c02290,10.1055/s-0040-1720350,10.1039/d1qo00148e,10.1016/j.tet.2020.131757,10.1021/acs.joc.0c01632,10.1039/d0gc01194k,10.1021/acscatal.0c01232,10.1055/s-0039-1690717,10.1021/acs.organomet.9b00672,10.1002/aoc.5291,10.1080/00397911.2019.1695838,10.1039/c9nj01635j,10.1134/S1070428019070017,10.1021/acs.orglett.8b04030,10.6023/cjoc201809037,10.1002/anie.201809112,10.1002/ejoc.201801132,10.1039/c8qo00799c,10.1016/j.ica.2017.06.039,10.1002/ajoc.201700464,10.1016/j.tet.2017.05.090,10.1039/c7ra04817c,10.1021/acs.orglett.6b02981,10.1002/adsc.201600686,10.1021/acs.joc.6b00616,10.1002/adsc.201501138,10.1002/ejoc.201501559,10.1039/c5ra26182a,10.1002/anie.201507623,10.1002/chem.201502329,10.1002/ejoc.201500734,10.1002/anie.201411402,10.1107/S2053229615001680,10.1071/CH15459,10.1039/c5ra09631f,10.1021/ie501081q,10.1016/j.tetlet.2014.10.077,10.1080/00397911.2014.945187,10.1002/adsc.201400201,10.1021/ol4031364,10.1021/ja4076716,10.1055/s-0033-1339176,10.1016/j.tet.2013.05.063,10.1002/cctc.201200592,10.1016/j.tetlet.2012.11.106,10.1039/c2gc36455g,10.1016/j.tetlet.2012.10.005,10.1016/j.inoche.2012.08.016,10.1002/adsc.201200280,10.1016/j.tet.2012.02.054,10.1021/ol300450j,10.1002/adsc.201100809,10.1007/3418_2011_15,10.1039/c1gc16174a,10.1007/3418_2011_10,10.1021/ja2092954,10.1021/ol202068p,10.1248/cpb.59.714,10.1021/cr100347k,10.1002/anie.201007733,10.1039/c1cc11930c,10.3390/molecules16010590,10.1039/c0sc00234h,10.1016/j.tet.2010.03.062,10.1021/jo1006152,10.1016/j.tetasy.2010.03.045,10.1016/j.tetlet.2010.02.015,10.1016/j.tet.2009.12.004,10.1007/978-3-642-12073-2_3,10.1055/s-0029-1218275,10.1055/s-2008-1078254,10.1002/ejoc.2008000073/14/2022
375
266FALSEol702499h10.1021/ol702499hhttps://sci-hub.wf/10.1021/ol702499hhttps://doi.org/10.1021/ol702499hNiC-O ActivationGerry7-MarTRUE394972007Knochel, P
Nickel(0) triethyl phosphite complex-catalyzed allylic substitution with retention of regio- and stereochemistry
ORGANIC LETTERS
Nickel(0) triethyl phosphite complex-promoted reaction of allylic acetates with thiols produced allylic sulfides with retention of configuration without allylic rearrangement. A similar reaction of allylic acetates with alcohols and phenols also proceeded with retention of regio- and stereochemistry.
12/20/2007Csp2_ar-Csp3E-NuOMgOTfMgXArylAlkylNo baseNo BaseWeak0.53_10.1002/anie.201100683,10.1021/ja202769t,10.1021/acs.joc.5b00135,10.1021/jo102446410.1021/acs.chemrev.9b00682,10.1002/ajoc.201900163,10.1021/acs.orglett.8b03417,10.1055/s-0037-1609941,10.3390/molecules23061449,10.1039/c6ra06748d,10.1002/chem.201501543,10.1002/anie.201502379,10.1002/anie.201411518,10.1021/acs.joc.5b00135,10.1021/jo500905m,10.1039/c3sc53047g,10.1007/s40242-013-3057-z,10.1002/adsc.201200369,10.1055/s-0031-1290972,10.1055/s-0031-1290765,10.1002/anie.201107017,10.1021/jo201630e,10.1021/ja202769t,10.1021/jo1024464,10.1021/ol200098d,10.1021/cr100259t,10.1021/cr100327p,10.1002/anie.201007187,10.1002/anie.201100683,10.1002/ijch.201000033,10.1021/jo101027h,10.1021/jo1001615,10.1002/anie.201000816,10.1021/ja902046m,10.1039/b805648j,10.1002/chem.200901913,10.1055/s-0028-1087418,10.1021/jo8015852,10.1016/j.tetlet.2008.03.096,10.1002/anie.200802292,10.1039/b807258b3/10/2022
376
396FALSEja401344e10.1021/ja401344ehttps://sci-hub.wf/10.1021/ja401344ehttps://doi.org/10.1021/ja401344eNiC-H ActivationElaine14-FebTRUE18927892013Chatani, N
Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance
J AM CHEM SOC
The alkylation of the ortho C-H bonds in benzamides and acrylamides containing an 8-aminoquinoline moiety as a bidentate directing group with unactivated alkyl halides using nickel complexes as catalysts is described. The reaction shows high functional group compatibility. In reactions of meta-substituted aromatic amides, the reaction proceeds in a highly selective manner at the less hindered C-H bond.
Osaka Univ4/10/2013TRUEFALSETRUEyCsp3-Csp2_arE-NuXHBrHAlkylArylNa2CO3Ionic-CO3_10.1002/anie.201511197,10.1021/acs.orglett.6b02166,10.1038/nature22813,10.1021/acs.orglett.6b00658,10.1039/c5cy01299f,10.1002/anie.201309584,10.1021/ja413131m,10.1021/ol501707z,10.1021/acs.joc.5b00669,10.1246/bcsj.20140387,10.1021/acscatal.7b01044,10.1002/anie.201510743,10.1002/ajoc.201700569,10.1039/c5sc02942b,10.1021/acs.organomet.6b00201,10.1021/acscatal.8b04267,10.1021/acscatal.6b01120,10.1039/d1cc02983e,10.1021/acscatal.6b02003,10.1039/c7qo00850c,10.1039/c9sc01446b,10.1021/ja5095342,10.1021/acs.orglett.6b02236,10.1002/anie.201709087,10.1039/c4cc00716f,10.1039/c6qo00149a,10.1039/c5cc01436k10.1007/s11030-022-10403-x,10.1039/d2qo00161f,10.1039/d1qo01676h,10.1021/acs.chemrev.1c00519,10.1039/d1qo01508g,10.1002/adsc.202100992,10.1039/d1cc03589d,10.1021/acs.orglett.1c01832,10.1021/acs.joc.1c00685,10.1039/d0cs01441a,10.1039/d1cc02983e,10.1021/acs.orglett.1c01821,10.1039/d1sc02785a,10.1039/d1ra03992j,10.1021/acs.orglett.1c01103,10.1021/acs.orglett.1c01253,11210..DOI:10.1002/cjoc.20220000680,10.1039/d0cs01107j,10.1021/jacs.1c00237,10.1039/d0sc05813k,10.1021/acscatal.0c05580,10.1016/j.tetlet.2021.152825,10.1021/acscatal.0c04205,10.1021/acs.orglett.0c03688,10.1016/j.jscs.2020.101178,10.1021/acs.joc.0c02631,10.1021/acs.joc.0c02069,10.1021/acs.orglett.0c03126,10.1039/d0cc05491g,10.1021/acs.orglett.0c02241,10.1039/d0cc02851g,10.1002/anie.202004958,10.1055/s-0037-1610756,10.1016/j.tet.2020.131201,10.1039/d0ob00557f,10.1080/00397911.2020.1761392,10.1021/jacs.0c01629,10.1002/cjoc.201900468,10.1039/d0cc01254h,10.1002/bkcs.11996,10.1021/acs.chemrev.9b00495,10.1002/anie.201913930,10.1021/acs.orglett.9b03158,10.1039/c9sc03758f,10.1039/c9cc07466j,10.1038/s41467-019-13098-1,10.1039/c9sc01446b,10.1021/acs.orglett.9b02717,10.1002/anie.201906658,10.1002/tcr.201800093,10.1016/j.trechm.2019.06.002,10.1002/chem.201900543,10.1002/cssc.201900151,10.1021/acs.orglett.9b01846,10.1002/cjoc.201900090,10.1002/anie.201808159,10.1021/jacs.9b02411,10.1002/ajoc.201900109,10.1002/anie.201806629,10.1021/acs.organomet.9b00195,10.1039/c9ob00648f,10.1021/acscatal.8b04415,10.1039/c9ob00243j,10.1039/c9cy00009g,10.1021/acs.organomet.8b00899,10.3390/molecules24071234,10.1039/c8sc05063e,10.1021/acs.orglett.9b00351,10.1038/s42004-019-0132-5,10.1039/c8qo01274a,10.1021/acsomega.9b00030,10.1021/acs.chemrev.8b00507,10.6023/cjoc201808023,10.1002/cctc.201801625,10.1039/c9ra00749k,10.1002/ajoc.201800664,10.1021/acscatal.8b04267,10.1007/s00706-018-2305-9,10.1002/ejoc.201801353,10.1039/c8sc03606c,10.1039/c8ob02237b,10.1021/acscatal.8b03770,10.1021/acs.joc.8b02197,10.1002/anie.201712520,10.1039/c8ob01712c,10.1002/anie.201807664,10.21577/0100-4042.20170269,10.1039/c8cc05026k,10.1021/acs.orglett.8b02109,10.1021/acscatal.8b01675,10.1016/j.tet.2018.04.029,10.1039/c8sc01741g,10.1002/ejic.201800168,10.1021/acs.organomet.8b00025,10.6023/cjoc201708055,10.1039/c7qo00850c,10.1039/c7sc04604a,10.1002/anie.201711968,10.1246/bcsj.20170316,10.1002/ajoc.201700569,10.1039/c7dt03403b,10.1002/anie.201709087,10.1021/acs.orglett.7b02968,10.1002/ijch.201700044,10.1016/j.ccr.2017.06.018,10.1039/c7qo00625j,10.1021/acscatal.7b02394,10.1021/acs.joc.7b02220,10.1021/acs.orglett.7b02823,10.1021/acs.chemrev.6b00833,10.1039/c7cc05532c,10.1039/c7sc01750b,10.1055/s-0036-1589010,10.1002/chem.201702168,10.1002/chem.201703191,10.1039/c7ob01353a,10.1039/c7cc05011a,10.1002/adsc.201700186,10.1039/c7sc01732d,10.1021/jacs.7b03548,10.1021/acs.joc.7b00582,10.1002/chem.201605657,10.1021/jacs.7b05574,10.1021/acs.joc.7b00535,10.1038/nature22813,10.1002/adsc.201700290,10.1002/cssc.201700452,10.1021/acscatal.7b01044,10.1002/cssc.201700321,10.1021/acscatal.7b00247,10.1039/c6sc05622a,10.1039/c7cc01097d,10.1021/acscatal.7b00094,10.1055/s-0036-1588123,10.1021/acs.orglett.6b03856,10.1039/c7ob00022g,10.1021/acscatal.6b03277,10.1021/jacs.6b10309,10.1021/jacs.6b10303,10.1039/c6qo00479b,10.1039/c6ob02224c,10.1002/ejoc.201601061,10.1007/s40010-016-0289-6,10.1021/acs.organomet.6b00655,10.1002/ejoc.201600955,10.1021/acscatal.6b02477,10.1016/j.jorganchem.2016.08.026,10.1002/chem.201604344,10.1002/ejoc.201601045,10.1021/acs.joc.6b01725,10.1021/acs.joc.6b01702,10.1021/acs.orglett.6b02166,10.1021/jacs.6b06862,10.1021/jacs.6b04789,10.1055/s-0035-1562509,10.1007/s41061-016-0059-6,10.1016/j.tet.2016.08.026,10.1002/anie.201604956,10.1021/acs.orglett.6b02236,10.1021/acscatal.6b02003,10.1039/c6cc05330k,10.1021/jacs.6b06908,10.1021/acs.inorgchem.6b01162,10.1002/chem.201602513,10.1021/acscatal.6b01816,10.1007/s41061-016-0053-z,10.1002/adsc.201600177,10.1021/acscatal.6b01120,10.1021/acscatal.6b00964,10.1002/anie.201601560,10.1002/anie.201601999,10.1021/acs.orglett.6b01288,10.1021/acs.organomet.6b00201,10.1002/adsc.201600080,10.1021/acs.joc.6b00129,10.1021/jacs.6b02405,10.1021/acs.orglett.6b00846,10.1002/slct.201600296,10.1002/chem.201600229,10.1021/acs.orglett.6b00658,10.1021/acs.orglett.6b00217,10.1002/ejoc.201501551,10.1002/anie.201510743,10.1002/anie.201511197,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102013FALSEFALSEFALSEFALSE135145308
377
66FALSEol800335v10.1021/ol800335vhttps://sci-hub.wf/10.1021/ol800335vhttps://doi.org/10.1021/ol800335vNiC-O ActivationGerryTRUE371602008Yorimitsu, H
Direct aminoalkylation of arenes and hetarenes via Ni-Catalyzed Negishi cross-coupling reactions
ORGANIC LETTERS
A direct room-temperature Ni-catalyzed cross-coupling of aminoalkylzinc halides, readily available from the corresponding aminoalkyl chlorides via Grignard reagents, with aryl and hetaryl electrophiles, allows a convenient one-step preparation of aminoalkyl (het)arenes, bearing a basic tertiary nitrogen in the side chain, including piperidine and tropane derivatives. Such aminoalkylarene scaffolds are widely present in various biologically active molecules.
Kyoto Univ4/17/2008Csp3-Csp3E-NuOCsp3OBoc
C(OH)(Me)2
AllylAllylNo baseNo BaseMedium0.31_10.6023/cjoc202106021,10.1021/acs.orglett.1c02938,10.1039/d1sc02547c,10.1021/acs.chemrev.0c00157,10.1039/d0cc02697b,10.1002/anie.201915454,10.1021/jacs.9b12343,10.1039/c8sc04505d,10.1021/acs.orglett.8b03627,10.1039/c8cs00253c,10.2174/1570193X15666180220125122,10.1021/acs.organomet.6b00238,10.1055/s-0034-1380418,10.1021/acs.orglett.5b01127,10.1039/c5cc04085j,10.1002/anie.201406077,10.1021/ol501887a,10.1021/ol500456s,10.1021/ja312487r,10.1039/c3ra41690a,10.1002/ejoc.201101616,10.1002/adsc.201100770,10.1039/c2cc33641c,10.1039/c2sc00923d,10.1007/3418_2011_15,10.1021/ja2075967,10.1021/ja205717f,10.1002/anie.201100631,10.1039/c0cc01950j,10.1039/c1cc13348a,10.1039/c0nj01019g,10.1021/ol100599c,10.1021/ol1002576,10.1002/anie.201001752,10.1246/bcsj.82.778,10.3987/COM-08-S(D)3,10.1002/chem.2009022211/25/2022
378
398FALSEnature1461510.1038/nature14615https://sci-hub.wf/10.1038/nature14615https://doi.org/10.1038/nature14615NiC-N ActivationKellyTRUE355261222015Houk, KN
Conversion of amides to esters by the nickel-catalysed activation of amide C-N bondsNATURE
Amides are common functional groups that have been studied for more than a century(1). They are the key building blocks of proteins and are present in a broad range of other natural and synthetic compounds. Amides are known to be poor electrophiles, which is typically attributed to the resonance stability of the amide bond(1,2). Although amides can readily be cleaved by enzymes such as proteases(3), it is difficult to selectively break the carbon-nitrogen bond of an amide using synthetic chemistry. Here we demonstrate that amide carbon-nitrogen bonds can be activated and cleaved using nickel catalysts. We use this methodology to convert amides to esters, which is a challenging and underdeveloped transformation. The reaction methodology proceeds under exceptionally mild reaction conditions, and avoids the use of a large excess of an alcohol nucleophile. Density functional theory calculations provide insight into the thermodynamics and catalytic cycle of the amide-to-ester transformation. Our results provide a way to harness amide functional groups as synthetic building blocks and are expected to lead to the further use of amides in the construction of carbon-heteroatom or carbon-carbon bonds using non-precious-metal catalysis.
Univ Calif Los Angeles
8/6/2015TRUEFALSEFALSEyyCsp2-Osp2E-NuNH
N(Bn)Boc
H
Carbonyl
ORNo baseNo 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62015FALSEFALSEFALSEFALSE524756379
379
172FALSEol801972f10.1021/ol801972fhttps://sci-hub.wf/10.1021/ol801972fhttps://doi.org/10.1021/ol801972fNiC-O ActivationLongTRUE9091062008Percec, V
Nickel-catalyzed allylation of allyl carbonates with homoallyl alcohols via retro-allylation providing 1,5-hexadienes
ORGANIC LETTERS
A highly efficient and mild method for the synthesis of 1,5-hexadienes, nickel-catalyzed reactions of Boc-protected allyl alcohols with homoallyl alcohols, has been developed. Nickel-mediated retro-allylation allows for the use of homoallyl alcohols as allylmetal equivalents in the synthesis of 1,5-hexadienes.
Univ Penn11/6/2008Csp2_ar-Csp2_arE-NuOBOTsB(nep)ArylArylK3PO4Ionic-PO4Weak0.36TMxx10.1002/ejoc.201001519,10.1021/ol401727y,10.1002/ejoc.201200444,10.1021/jo202037x,10.1002/adsc.201100151,10.1002/adsc.201000710,10.1021/jo3001194,10.1002/ejoc.201000147,10.1021/jo202298210.1016/j.ccr.2021.214165,10.1039/d1nj03706d,10.1002/aoc.6378,10.1002/tcr.202100142,10.1039/d1ra01940f,10.1002/ejoc.202001382,10.1002/chem.202004132,10.1021/acs.chemrev.0c00088,10.1021/acs.joc.0c00929,10.1021/acs.chemrev.9b00682,10.1021/acs.biomac.0c00507,10.1021/acs.biomac.9b01765,10.1021/acs.biomac.9b01282,10.1039/c9ob01244c,10.1002/chem.201900937,10.1016/j.tet.2018.10.025,10.1039/c8nj02184h,10.1007/s11705-017-1669-4,10.1021/acs.joc.7b02033,10.1002/open.201700036,10.1055/s-0035-1562342,10.1055/s-0035-1562343,10.1002/cctc.201600456,10.1021/acs.organomet.6b00161,10.1002/chem.201503926,10.1002/ejic.201500852,10.1002/ejoc.201500987,10.1055/s-0035-1560712,10.1016/j.jorganchem.2015.04.017,10.1016/j.jorganchem.2015.04.019,10.1002/adsc.201401153,10.1246/cl.141084,10.1016/j.catcom.2014.08.037,10.1039/c5ob00545k,10.1002/ejoc.201402881,10.1021/ol502120q,10.1016/j.tet.2014.03.076,10.1002/chem.201304861,10.6023/cjoc201307035,10.1002/chem.201302677,10.1021/ol401727y,10.1021/jo401104y,10.1002/pola.26573,10.1039/c3dt51119g,10.1039/c3ra22905j,10.1039/c3cs35521g,10.1002/adsc.201200364,10.1021/jo301270t,10.3987/REV-12-736,10.1002/ejoc.201200444,10.1002/ejoc.201200368,10.1021/ol300950r,10.1055/s-0031-1289747,10.1021/jo3001194,10.1021/jo2022982,10.1039/c2dt30118k,10.1021/jo202037x,10.1002/chem.201100967,10.1021/ol202267t,10.1002/adsc.201100151,10.1246/cl.2011.702,10.1021/om200115y,10.1002/chem.201100361,10.1021/jo2003488,10.1016/j.tetlet.2010.11.133,10.1002/ejoc.201001519,10.1021/cr100259t,10.1002/adsc.201000710,10.1002/chem.201001943,10.1002/chem.201002273,10.1021/jo101718v,10.1021/jo101023t,10.1002/ejoc.201000147,10.1021/om9010802,10.1021/ja910808x,10.3987/COM-09-S(S)63,10.1021/ja907882n,10.1021/ol902155e,10.1021/ol9015892,10.1021/ol802493z,10.1002/anie.200901879checked by Kelly12/10/2021
380
189FALSEol901217m10.1021/ol901217mhttps://sci-hub.wf/10.1021/ol901217mhttps://doi.org/10.1021/ol901217mNiC-O ActivationKellyTRUE1037282009Shi, ZJ
Two-Step, One-Pot Ni-Catalyzed Neopentylglycolborylation and Complementary Pd/Ni-Catalyzed Cross-Coupling with Aryl Halides, Mesylates, and Tosylates
ORGANIC LETTERS
Two-step, one-pot neopentylglycolborylation of aryl iodides and bromides catalyzed by NiCl2(dppe) and NiCl2(dppp) is reported. Electron-rich and electron-deficient aryl neopentylglycolboronates were efficiently cross-coupled with aryl iodides, bromides, chlorides, mesylates, and tosylates by exploiting complementary Pd/Ni and Ni/Ni catalysis. The borylation route was further extended to a three-step, one-pot synthesis of biaryls via in situ Ni-catalyzed borylation and Pd-mediated cross-coupling.
Peking Univ8/6/2009Csp2_ar-Csp2_arE-NuOMgOMeMgXArylArylNo baseNo BaseStrong-0.28_10.1021/ol901978e,10.1021/jo2000034,10.1021/ja200398c,10.1021/ja907700e,10.1002/ejoc.201001519,10.1021/jacs.6b11412,10.1021/ol401175710.1055/s-0041-1737882,10.1002/ajoc.202100591,10.1021/acs.orglett.1c03048,10.1039/d1ob01707a,10.1002/adsc.202100641,10.1039/c9cs00571d,10.1039/d0cc07743g,10.1021/acs.chemrev.0c00301,10.1039/d0gc03411h,10.1039/d0ra08068c,10.1021/acscatal.0c03903,10.1021/acsomega.0c03415,10.1039/d0ra05251e,10.1039/d0sc01229g,10.1002/adsc.202000531,10.1021/acs.joc.0c00458,10.6023/cjoc202002035,10.1039/d0sc01641a,10.1055/s-0039-1690045,10.1039/c9nj05114g,10.1039/c9gc02694k,10.1002/ejoc.201901364,10.1021/acs.organomet.9b00543,10.1021/jacs.9b02312,10.1021/acs.orglett.9b00875,10.1039/c8nj05503c,10.1021/acs.joc.8b02150,10.1021/acscatal.8b00933,10.1002/cjoc.201700773,10.1055/s-0036-1591523,10.1021/acs.orglett.7b01938,10.1016/j.tetlet.2017.06.055,10.1021/jacs.6b11412,10.1021/acs.orglett.6b03306,10.1021/jacs.6b01656,10.1002/chem.201604061,10.1021/acssuschemeng.6b00729,10.1002/adsc.201600590,10.1002/adsc.201500822,10.1021/acs.joc.5b02077,10.1016/bs.adomc.2016.07.001,10.1039/c5sc03359d,10.1002/kin.20966,10.1016/j.tetlet.2015.11.025,10.1021/acs.joc.5b01977,10.1021/acs.chemrev.5b00138,10.1021/acs.orglett.5b02380,10.1038/ncomms8508,10.1021/ar500345f,10.1039/c5ra13137e,10.1002/hc.21189,10.1021/cr400628s,10.1055/s-0033-1339114,10.1246/bcsj.20130332,10.1002/anie.201309546,10.1039/c4ra08675a,10.1007/128_2013_494,10.1039/c4cs00206g,10.1039/c3ra45178j,10.1002/chem.201303637,10.1016/j.tet.2013.09.060,10.1016/j.jorganchem.2013.07.068,10.1002/anie.201303376,10.1021/ol4011757,10.6023/cjoc201212033,10.1021/op300301u,10.1021/ol303546p,10.1021/om301263s,10.1002/ajoc.201200185,10.1016/j.poly.2012.09.030,10.1021/jo302307y,10.1039/c3cc44562c,10.1039/c3cs35521g,10.1016/j.tetlet.2012.09.072,10.1246/bcsj.20120081,10.1002/adsc.201200369,10.1002/adsc.201100836,10.1021/ja211389g,10.1021/ja207759e,10.1016/j.jorganchem.2011.07.047,10.1002/chem.201101930,10.1021/ol2012007,10.1021/ja200398c,10.1021/jo2000034,10.1002/ejoc.201001519,10.1021/cr100259t,10.1021/cr1002276,10.1021/jo101718v,10.1246/cl.2010.1050,10.1021/ol1018739,10.5012/bkcs.2010.31.03.582,10.1021/ja907700e,10.1021/ol901978eKelly2/7/2022
381
82FALSEol901429g10.1021/ol901429ghttps://sci-hub.wf/10.1021/ol901429ghttps://doi.org/10.1021/ol901429gNiC-O ActivationGerryTRUE461162009Pineschi, M
Carbon-Carbon Formation via Ni-Catalyzed Suzuki-Miyaura Coupling through C-CN Bond Cleavage of Aryl Nitrile
ORGANIC LETTERS
The Suzuki-Miyaura coupling of aryl nitriles with aryl/alkenyl boronic esters is reported. With this method, the cyano group could be applied as a protecting group of arenes and finally as a leaving group to further construct polyaryl scaffolds.
Univ Pisa8/20/2009Csp3-Csp3E-NuOH
O(Ring-Opening)
HAlkylAlkylIonic-PO4Weak1_10.1002/ejic.202100820,10.1021/acs.chemrev.1c00255,10.1016/j.ccr.2021.214165,10.1039/d1qo00100k,10.1002/adsc.202001493,10.1021/acs.chemrev.9b00384,10.1002/chem.202000289,10.1021/acs.chemrev.9b00682,10.1002/ejoc.201901853,10.1021/acs.orglett.9b03672,10.1002/chem.201901406,10.1021/jacs.9b03991,10.1002/anie.201809919,10.1055/s-0036-1589164,10.1021/jacs.7b12160,10.1039/c7gc02282d,10.1039/c6cc07924e,10.1039/c7ra09006d,10.1021/acs.organomet.6b00652,10.1021/acscatal.6b02208,10.1021/acs.chemrev.6b00193,10.1039/c6sc01120a,10.1021/acs.orglett.5b02194,10.1021/jacs.5b04404,10.2174/138527281909150507104019,10.1021/cr400543u,10.1021/cr400709j,10.1055/s-0033-1339032,10.1021/ja504625m,10.1021/ja412547r,10.1039/c4cc01312c,10.1039/c3ob41328d,10.1002/anie.201305098,10.1002/cctc.201200592,10.1021/ol3001552,10.1039/c2ob07107j,10.1007/3418_2011_15,10.1002/asia.201000875,10.3762/bjoc.7.95,10.1016/j.tet.2010.10.075,10.1002/anie.201100613,10.1021/jo100407s,10.1002/anie.2009059931/25/2022
382
403FALSEjo070313d10.1021/jo070313dhttps://sci-hub.wf/10.1021/jo070313dhttps://doi.org/10.1021/jo070313dNiC-H ActivationGerry21-FebTRUE2149#N/A2007Hara, K
Nickel−NHC-Catalyzed α-Arylation of Acyclic Ketones and Amination of Haloarenes and Unexpected Preferential N-Arylation of 4-AminopropiophenoneJ ORG CHEM
Arylation of both acyclic ketones and primary and secondary amines was achieved using a new, simple, stable, and easy-to-access nickel(II)−halide complex bearing mixed PPh3/N-heterocyclic carbene ligands as a catalyst precursor. Acyclic ketones were first arylated at the α-position with the nickel catalyst. On the other hand, less basic amines, such as diphenylamine and 4-aminobenzophenone, were more favorable in the catalytic amination of haloarenes than basic amines, contrary to previous reports. N-Arylation of 4-aminopropiophenone was found to proceed selectively without causing α-arylation of the ketone group.
7/6/2007Csp3-Csp2_arE-NuHXHXAlkylArylIonic-OtBuNu-H_10.1021/acs.organomet.5b00874,10.1002/anie.201410875,10.1021/acscatal.7b03079,10.1002/anie.201403823,10.1039/c6ob01299j,10.1002/chem.201406457,10.1021/ol403209k,10.1039/c4cc00959b,10.1021/jo702255810.1002/tcr.202100204,10.1002/ejoc.202100194,10.1039/d1cc00913c,10.1039/d0qi01411g,10.1021/acs.orglett.1c00463,10.1016/j.jorganchem.2021.121754,10.1002/anie.202012877,10.1021/acs.joc.0c02209,10.1016/j.tetlet.2020.152605,10.1021/acscatal.0c00221,10.1016/j.ccr.2019.03.006,10.1055/s-0037-1610843,10.1055/s-0037-1609963,10.1080/00397911.2017.1410175,10.1021/acscatal.7b03079,10.1002/anie.201707906,10.1007/s11172-017-1920-7,10.1039/c7dt01805c,10.1021/acs.organomet.6b00906,10.1016/j.cclet.2016.11.002,10.1016/j.jorganchem.2016.12.029,10.1002/anie.201606979,10.1002/tcr.201500305,10.1039/c6nj01118g,10.1021/acscatal.5b02021,10.1039/c6ob01299j,10.1039/c6dt02995g,10.1021/acs.organomet.5b00874,10.1002/ejoc.201500962,10.1016/j.jorganchem.2015.07.015,10.1055/s-0034-1380813,10.1016/j.tetlet.2015.02.061,10.1016/j.ica.2014.11.005,10.1002/anie.201410875,10.1002/chem.201406457,10.1016/j.molcata.2014.10.031,10.1021/cs5014927,10.3906/kim-1408-33,10.1021/om500593s,10.5059/yukigoseikyokaishi.72.1110,10.1002/adsc.201400201,10.1002/anie.201403823,10.1002/ejoc.201402022,10.1021/ol403209k,10.1039/c3ob42053a,10.1039/c4cc00959b,10.1021/om4004863,10.1002/adsc.201300444,10.1002/adsc.201300207,10.1002/chem.201202798,10.1039/c3dt00086a,10.1016/j.jorganchem.2012.08.027,10.1016/j.tet.2012.07.084,10.1002/adsc.201200389,10.1021/ol3021836,10.1002/ejic.201200095,10.1021/om201101g,10.1021/om200937d,10.1021/om200864z,10.1246/cl.2011.1036,10.1016/j.ica.2010.12.004,10.1021/ol200964m,10.1021/om200246k,10.1021/om200090d,10.1021/om1011984,10.1021/jo1021426,10.3762/bjoc.7.10,10.1002/adsc.201000223,10.1016/S1872-2067(09)60089-9,10.1016/j.tet.2009.12.043,10.1021/cr9000836,10.1002/ejic.200900843,10.1002/anie.200903424,10.1039/b924716e,10.1039/c0dt00021c,10.1016/j.poly.2009.05.080,10.1021/cr900074m,10.1039/b911286c,10.1070/RC2009v078n11ABEH004021,10.1021/om800711g,10.1021/om800488x,10.1016/j.jorganchem.2008.07.026,10.1021/om800376q,10.1021/om8001125,10.1021/jo70225582/28/2022
383
404FALSEjacs.5b0294510.1021/jacs.5b02945https://sci-hub.wf/10.1021/jacs.5b02945https://doi.org/10.1021/jacs.5b02945NiC-H ActivationGerry23-FebTRUE895#N/A2015Helquist, P
Ni-Catalyzed Alkenylation of Ketone Enolates under Mild Conditions: Catalyst Identification and Optimization
CHEM COMMUN
A procedure for Ni-catalyzed cross-coupling of ketone enolates with alkenyl halides has been developed. Intermolecular coupling of aromatic and aliphatic ketone lithium enolates with a variety of alkenyl halides is achieved in the presence of Ni(cod)2 catalyst (5 mol %), an N-heterocyclic carbene (NHC) ligand, and LiI (10 mol %) at 6–22 °C for 0.5–12 h with yields of up to 90%. During the initial development of this reaction, a misleading result with respect to the actual active catalyst was obtained using commercially available Q-Phos ligand, which was found to contain a trace of Pd metal contaminant sufficient to catalyze the reaction. However, under the final conditions optimized for Ni(cod)2 in the presence of an NHC ligand, Pd was incompetent as a catalyst.
6/10/2015Csp3-Csp2E-NuHXHBrAlkylVinylIonicNitrogen(neutral)Nu-H_10.1002/anie.201712693,10.1021/acs.orglett.8b02256,10.1039/c5sc03704b,10.1039/c5sc01589h,10.1039/c6ob01299j10.1039/d1cc02576g,10.1016/j.tetlet.2021.153129,10.1002/adsc.202100260,10.1039/d1sc01483h,10.1039/d1cc00913c,10.1021/acs.accounts.0c00809,10.1002/cjoc.202000475,10.1039/c9gc01766f,10.1002/anie.201906213,10.1021/jacs.9b03751,10.1021/acs.orglett.8b03705,10.1021/acs.orglett.8b02256,10.1055/s-0037-1609963,10.1002/anie.201713278,10.1021/acscatal.7b04105,10.1002/anie.201712693,10.1021/acs.joc.7b02461,10.1016/j.ccr.2016.12.021,10.1002/anie.201703706,10.1002/anie.201703174,10.1021/acs.organomet.6b00769,10.1039/c6cc08392g,10.1021/acs.orglett.6b02969,10.1021/jacs.6b06847,10.1021/acs.orglett.6b01955,10.1016/j.tetlet.2016.04.033,10.1021/acs.orglett.6b00815,10.1039/c6ob02269c,10.1039/c6ob01299j,10.1039/c6gc00017g,10.1039/c5ob02397a,10.1039/c5sc03704b,10.1021/acscatal.5b02089,10.1021/jacs.5b11129,10.1021/acs.orglett.5b03020,10.1002/anie.201505895,10.1021/acs.orglett.5b01662,10.1039/c5sc01589h2/28/2022
384
186FALSEol901978e10.1021/ol901978ehttps://sci-hub.wf/10.1021/ol901978ehttps://doi.org/10.1021/ol901978eNiC-O ActivationShihongTRUE9823892009Chatani, N
Nickel-Catalyzed Borylative Ring Opening of Vinyl Epoxides and Aziridines
ORGANIC LETTERS
A mild ring opening of vinyl epoxides and aziridines with B(2)Pin(2) catalyzed by Ni(O)-Binap affords new functionalized allylic boron derivatives which undergo sequential transformations. The uncatalyzed allylation of aldehydes allows obtaining challenging bishomoallylic alicyclic 1,3-diols and 1,3-amino alcohols with remarkably high stereoselectivities. Valuable trans-bisallylic 1,4-amino alcohols can be obtained by a simple oxidation.
Osaka Univ11/5/2009Csp2-Csp2_arE-NuOBOMeB(nep)VinylArylCsFIonic-FStrong-0.28_10.1021/ja2084509,10.1021/acscatal.6b00801,10.1002/chem.201103784,10.1021/acs.joc.6b01627,10.1021/ol401727y,10.1021/jacs.8b02134,10.1021/acs.orglett.5b03151,10.1021/jacs.7b04279,10.1021/jacs.1c08399,10.1021/ol502583h,10.1002/anie.200907359,10.1021/jacs.6b11412,10.1021/ol4011757,10.1002/anie.201607646,10.1021/ol9028308,10.1039/c4cc08187k,10.1002/anie.200907287,10.1016/j.tet.2012.04.005,10.1021/jacs.7b04973,10.1021/ol4031815,10.1021/acs.orglett.5b02200,10.1021/ol503707m,10.1246/cl.15093610.1021/jacs.1c08399,10.1002/adsc.202100585,10.1002/hlca.202100089,10.1021/acs.orglett.1c01447,10.1039/c9cs00571d,10.1002/asia.202100277,10.1039/d0ra10248b,10.1039/d0ob02011g,10.1002/chem.202004132,10.1016/j.molstruc.2020.128572,10.1021/acs.orglett.0c02236,10.1016/j.mcat.2020.110915,10.1039/d0ra04362a,10.1016/j.isci.2020.100966,10.1002/anie.201913062,10.1021/acs.orglett.9b03170,10.1002/cjoc.201800554,10.1021/jacs.9b02312,10.1002/anie.201902315,10.1002/cjoc.201800575,10.1021/acs.orglett.9b00946,10.1021/acs.organomet.8b00720,10.1021/acs.orglett.8b03040,10.1021/acscatal.8b01286,10.1021/acs.orglett.8b00313,10.1021/acs.orglett.8b00674,10.1021/jacs.8b02134,10.1055/s-0036-1590985,10.1021/jacs.7b04973,10.1021/jacs.7b04279,10.1055/s-0036-1588705,10.1021/jacs.6b11412,10.1002/anie.201607646,10.1002/ajoc.201600411,10.1246/cl.160712,10.1021/acs.joc.6b01627,10.1002/asia.201600972,10.1002/chem.201602150,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1016/j.tet.2016.02.069,10.1002/adsc.201500721,10.1016/bs.adomc.2016.07.001,10.1021/acs.orglett.5b03151,10.1246/cl.150936,10.1002/chem.201502114,10.1021/acs.orglett.5b02200,10.1016/j.tet.2015.05.068,10.1021/acs.accounts.5b00051,10.1246/cl.141084,10.1021/ol503707m,10.1039/c5qo00039d,10.1039/c4cc08187k,10.1021/ol502583h,10.1021/jo5022234,10.1021/ja5043534,10.1016/j.tetlet.2013.12.083,10.1039/c4cs00206g,10.1002/ejoc.201301372,10.1021/ol4031815,10.1021/ol401727y,10.1021/ol4011757,10.1002/cjoc.201300340,10.1021/ja312464b,10.1021/ja311940s,10.1007/3418_2012_42,10.1039/c3ob27128e,10.1039/c3cs35521g,10.1016/j.tet.2012.04.005,10.1021/ol3009842,10.1021/jo3005149,10.1002/chem.201103784,10.1021/ja2084509,10.1002/anie.201203778,10.1021/ja207759e,10.2174/157017911796957357,10.1246/cl.2011.1001,10.1021/ol2012007,10.1021/cr100259t,10.1021/cr1002276,10.1021/ol102825t,10.1021/ja1097385,10.1002/anie.201103599,10.1039/c0cc05169a,10.1002/chem.201002273,10.1021/jo1007898,10.1016/j.jorganchem.2010.02.007,10.1021/ol9028308,10.1002/anie.200907287,10.1002/anie.200907359Kelly12/1/2021
385
93FALSEol902830810.1021/ol9028308https://sci-hub.wf/10.1021/ol9028308https://doi.org/10.1021/ol9028308NiC-O ActivationLongTRUE4910282010Shi, ZJ
Nickel-Catalyzed Cross-Coupling Reaction of Alkenyl Methyl Ethers with Aryl Boronic Esters
ORGANIC LETTERS
The Ni(0)-catalyzed cross-coupling of alkenyl methyl ethers with boronic esters is described. Several types of alkenyl methyl ethers can be coupled with a wide range of boronic esters to give the stilbene derivatives.
Peking Univ1/15/2010Csp2_ar-Csp2_arE-NuOMg
OSO2OPh
MgXArylArylNo baseNo BaseWeak0.7_10.1021/acs.joc.6b01627,10.1021/acs.orglett.6b02656,10.1021/jo300547v,10.1002/chem.201103050,10.1021/ol4011757,10.1021/om300566m,10.1021/jo501291y,10.1021/jo1024464,10.1002/anie.201101461,10.1002/ejoc.20120044410.1055/a-1349-3543,10.1002/anie.202007211,10.1002/ejoc.201901471,10.1016/j.tet.2018.10.025,10.1021/acs.joc.8b01762,10.1070/RCR4795,10.1021/acs.joc.7b01377,10.1016/j.ejmech.2016.09.031,10.1021/acs.orglett.6b02656,10.1002/jhet.2513,10.1021/acs.joc.6b01627,10.1002/ejoc.201600242,10.1002/ps.4055,10.1039/c6qo00336b,10.1055/s-0035-1560175,10.1002/ejoc.201500987,10.1002/adsc.201500304,10.1002/ajoc.201500044,10.1002/aoc.3289,10.1021/acs.jpca.5b00569,10.1039/C5QO00243E,10.1021/jo502172c,10.1007/s11426-014-5138-3,10.1021/jo501291y,10.1515/pac-2014-5038,10.1021/cs4009946,10.1002/ejoc.201300967,10.1021/ol401341s,10.1021/ol4011757,10.1039/c3ra44884c,10.1007/s00706-012-0838-x,10.1021/om300566m,10.1021/jo300547v,10.1002/ejoc.201200444,10.1021/ol300671y,10.1002/chem.201103050,10.1246/cl.2011.1001,10.1021/jo1024464,10.1021/cr100259t,10.1002/anie.201101461,10.1039/c1cc14206b,10.1002/chem.201002273,10.1021/ar100082d,10.1021/ol1018739,10.1016/j.tetlet.2010.03.11012/10/2021
386
217FALSEol902953410.1021/ol9029534https://sci-hub.wf/10.1021/ol9029534https://doi.org/10.1021/ol9029534NiC-O ActivationShihongTRUE13727402010Li, BJ
Biaryl Construction through Kumada Coupling with Diaryl Sulfates as One-by-One Electrophiles under Mild Conditions
ORGANIC LETTERS
Diaryl sulfates were successfully applied as one-by-one organo electrophiles in Kumada coupling to construct biaryls with the emission of harmless inorganic salts.
Peking Univ2/19/2010Csp2-Csp2_arE-NuOB
OCONMe2
B(OH)2VinylArylK2CO3Ionic-CO3Medium0.31_10.1016/j.tet.2012.04.005,10.1002/anie.201101461,10.1002/ejoc.201200444,10.1021/ja2084509,10.1021/jo300547v,10.1021/jo1024464,10.1002/chem.201103050,10.1002/ejoc.201001519,10.1021/ol4011757,10.1002/ejoc.201000147,10.1002/adsc.201100151,10.1021/jo3001194,10.1021/om500452c,10.1039/c0cc03107k,10.1039/c4qo00321g,10.1021/jo2022982,10.1021/jo2000034,10.1021/jacs.7b04973,10.1021/acscatal.5b01021,10.1021/jo4005537,10.1002/chem.201003403,10.1021/ol101592r,10.1002/chem.201003731,10.1021/acs.joc.6b01627,10.1021/om300566m,10.1021/acs.orglett.6b01398,10.1021/acscatal.6b0080110.1039/c9cs00571d,10.1002/anie.202103465,10.1055/a-1349-3543,10.1021/acscatal.0c03334,10.1021/acs.joc.0c01732,10.1021/acs.chemrev.0c00088,10.1002/aoc.5662,10.1021/acs.orglett.0c01127,10.1002/cjoc.201900506,10.1021/acs.joc.9b03512,10.1002/anie.201915790,10.2174/1871530319666191202141209,10.1021/jacs.9b08586,10.1016/j.jcat.2019.07.026,10.1002/cjoc.201800554,10.1002/ejic.201900244,10.1007/s10600-019-02705-8,10.1007/3418_2018_19,10.3390/molecules23102417,10.1016/j.jorganchem.2018.01.019,10.1002/ejoc.201701142,10.1002/ajoc.201700342,10.1021/jacs.7b04973,10.1021/acscatal.6b02912,10.1038/s41570-017-0025,10.1002/ejoc.201601098,10.1021/acs.joc.6b01627,10.1002/chem.201602150,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1021/acs.orglett.6b01398,10.1002/anie.201601899,10.1021/acs.joc.6b00317,10.1021/acs.joc.5b02667,10.1021/acs.joc.5b02562,10.1021/acs.joc.5b02077,10.1016/bs.adomc.2016.07.001,10.1039/c5ra27859g,10.1039/c5ee03256c,10.1002/anie.201505699,10.1021/acs.organomet.5b00632,10.1002/ejoc.201500630,10.1021/acscatal.5b01021,10.1002/ejoc.201500610,10.1002/adsc.201500304,10.1021/acs.inorgchem.5b00893,10.1246/cl.141084,10.1021/ar500345f,10.1021/ja512498u,10.1039/c4qo00321g,10.1016/j.jorganchem.2014.09.032,10.1016/j.ica.2014.08.012,10.1021/om500452c,10.1021/ol5024344,10.1002/ejoc.201402919,10.1016/j.tet.2014.07.059,10.1016/j.tetlet.2014.01.148,10.1007/s11426-014-5138-3,10.3762/bjoc.10.109,10.1021/ol500258q,10.1515/pac-2014-5038,10.1021/cs4009946,10.6023/cjoc201307035,10.1039/c3dt53012d,10.1016/j.tet.2013.10.089,10.1016/j.tetlet.2013.10.111,10.1021/jo400949p,10.1021/ol4011757,10.1055/s-0032-1316904,10.1021/jo4005537,10.5560/ZNB.2013-2342,10.1002/ejoc.201201574,10.1021/jo3018878,10.1021/ic302153s,10.1021/ol303130j,10.1007/3418_2012_42,10.1039/c3sc22242j,10.1039/c3cs35521g,10.1002/ejoc.201200914,10.1021/op300236f,10.1039/c3ra23188g,10.1002/ejoc.201200918,10.1021/om300566m,10.1021/jo300547v,10.1021/ol301681z,10.1021/jo300713h,10.1002/ejoc.201200444,10.1002/ejoc.201200368,10.1016/j.tet.2012.04.005,10.1021/ol301275u,10.1021/jo3001194,10.1021/jo202577m,10.1021/jo2022982,10.1021/ja2084509,10.1039/c2cc33755j,10.1039/c2ob06821d,10.1039/c2cc18150a,10.1039/c2cc17744g,10.1002/chem.201103050,10.1021/ja207759e,10.1002/adsc.201100165,10.1246/cl.2011.1001,10.1246/cl.2011.907,10.1021/ol201469r,10.1002/adsc.201100151,10.1007/s12039-011-0092-5,10.1002/adsc.201100101,10.1002/chem.201003731,10.1021/jo2000034,10.1021/jo1024464,10.1002/chem.201003403,10.1002/ejoc.201001519,10.1016/j.tet.2010.11.042,10.1002/anie.201101461,10.1002/chem.201001943,10.1002/chem.201002273,10.1021/ar100082d,10.1246/cl.2010.1050,10.1021/ol101493m,10.1021/ol101592r,10.1016/j.tetlet.2010.03.110,10.1002/ejoc.201000147,10.1021/ja100783c,10.1002/anie.201001028,10.1002/anie.201003379,10.1039/c0cc03107kKelly11/25/2021
387
408FALSEc4cc00959b10.1039/c4cc00959bhttps://sci-hub.wf/10.1039/c4cc00959bhttps://doi.org/10.1039/c4cc00959bNiC-H ActivationGerry28-FebTRUE523#N/A2014
From acetone metalation to the catalytic α-arylation of acyclic ketones with NHC–nickel(ii) complexes
Chem. Commun.
Air-stable N-heterocyclic carbene–nickel(II) complexes at concentrations as low as 1 mol% exhibit high catalytic activity for the α-arylation of acyclic ketones and join a highly restricted list of nickel catalysts for this key reaction. Mechanistic investigations suggest a radical pathway.
3/10/2014Csp3-Csp2_arE-NuHXHXAlkylArylIonic-OtBuNu-H_10.1002/chem.201406457,10.1039/c6ob01299j,10.1002/anie.20200682610.1039/d0qi01411g,10.1016/j.jorganchem.2021.121754,10.3390/molecules26010188,10.1002/anie.202006826,10.1002/chem.202000289,10.1080/00958972.2020.1786543,10.1016/j.ica.2020.119494,10.3390/catal10040372,10.1080/10406638.2018.1450270,10.1016/j.ccr.2019.03.006,10.1002/jhet.3504,10.1021/acs.chemrev.8b00505,10.1016/j.tet.2018.11.057,10.3390/catal9010076,10.1016/j.mcat.2018.10.024,10.1039/c8dt03882a,10.1002/zaac.201800151,10.1055/s-0037-1609963,10.1021/acscatal.8b00856,10.1016/j.jelechem.2018.02.043,10.1016/j.mcat.2017.06.033,10.1002/ejic.201700397,10.1021/acs.organomet.7b00109,10.1021/acs.organomet.6b00906,10.1021/acs.joc.6b02666,10.1039/c6dt03944h,10.1016/j.jorganchem.2016.03.017,10.1016/j.jorganchem.2016.02.018,10.1039/c6ob01299j,10.1039/c5dt04663g,10.1039/c6dt00252h,10.1002/ejic.201500993,10.3762/bjoc.11.235,10.1002/ejic.201500852,10.1002/anie.201502332,10.1055/s-0034-1380813,10.1016/j.tetlet.2015.02.061,10.1016/j.ica.2014.11.005,10.1002/ajoc.201500048,10.1002/ejic.201500061,10.1002/chem.201406543,10.1021/ja511730k,10.1002/chem.201406457,10.1021/cs5014927,10.1016/j.poly.2014.12.009,10.1002/chem.201404618,10.1039/c4cc09524c,10.1002/chem.2014049003/9/2022
388
267FALSEom010949+10.1021/om010949+https://sci-hub.wf/10.1021/om010949+https://doi.org/10.1021/om010949+NiC-O ActivationLong8-MarTRUE1302392002Fort, Y
Nickel-Catalyzed Efficient and Practical Suzuki-Miyaura Coupling of Alkenyl and Aryl Carbamates with Aryl Boroxines
ORGANOMETALLICS
Suzuki-Miyaura coupling of unactivated alkenyl carbamates is described to construct polysubstituted olefins. The developed process is also suitable for heteroaromatic and even electron-rich aromatic carbamates.
4/15/2002Csp3-Csp2_arE-EOXONaClAlkylArylNo baseNo BaseStrong-0.32_10.1039/c3ob41989d,10.1021/jacs.9b0328010.1002/cctc.202101579,10.1002/ajoc.202100616,10.1016/j.mcat.2021.111953,10.1002/slct.202101755,10.1021/jacs.1c05661,10.1021/acs.joc.1c00573,10.1039/d0gc01649g,10.1016/j.ccr.2019.213038,10.1055/s-0037-1611898,10.1002/cssc.201900784,10.1016/j.ccr.2019.03.006,10.1055/s-0037-1610699,10.1002/ejoc.201900098,10.1039/c9ob00572b,10.1021/jacs.9b03280,10.1021/acs.orglett.9b00889,10.1016/j.tet.2019.01.015,10.1002/ejoc.201801385,10.1021/jacs.8b07597,10.1002/ejoc.201701478,10.1002/anie.201708800,10.1002/anie.201706534,10.1021/acs.orglett.7b02399,10.1002/chem.201701665,10.1016/j.tetlet.2017.03.016,10.1039/c6cc09575e,10.1016/j.tet.2017.01.002,10.1002/anie.201611495,10.1021/acs.joc.6b02222,10.1039/c6nj01118g,10.1002/anie.201601930,10.1002/slct.201600207,10.1021/acscatal.5b02021,10.1039/c6ob00193a,10.1021/acscatal.5b02089,10.1016/j.jorganchem.2015.07.015,10.1002/chem.201500652,10.1016/j.ica.2014.11.005,10.1016/j.tetlet.2015.04.014,10.1155/2015/912104,10.1039/c5dt01516b,10.1002/ejoc.201402625,10.1002/anie.201402695,10.1039/c4sc00006d,10.1039/c3ob41989d,10.1002/adsc.201300485,10.1002/jccs.201300134,10.1016/j.tetlet.2013.07.071,10.1021/es401183v,10.1021/ol401105x,10.1002/adsc.201300026,10.1016/j.jorganchem.2013.01.014,10.1039/c3cc46271d,10.2174/138527212804546705,10.1002/adsc.201200389,10.1021/es302188f,10.1021/am301394u,10.1002/chem.201201125,10.1016/j.tetlet.2012.05.054,10.1021/om201101g,10.1002/adsc.201100927,10.1002/jhet.845,10.1021/om200864z,10.1002/chem.201101557,10.1016/j.molcata.2011.04.001,10.1002/chem.201100909,10.1002/asia.201000601,10.1021/ja107703n,10.1021/om1003072,10.1016/S1872-2067(09)60089-9,10.1039/c0cc01335h,10.1039/c0cc01980a,10.1021/ol901825u,10.1021/cr900074m,10.1021/cr800388c,10.1002/ejic.200801149,10.1021/ja806545e,10.1016/j.jorganchem.2008.10.052,10.1002/tcr.20165,10.1080/00958970902939814,10.1021/om800004j,10.1016/j.jorganchem.2007.07.007,10.1016/j.tet.2007.03.061,10.1039/b706846h,10.1016/j.jorganchem.2006.02.042,10.1016/j.tet.2006.05.006,10.1021/om0602759,10.1021/om0604223,10.1002/jccs.200600130,10.1246/bcsj.79.981,10.1002/adsc.200505409,10.1021/jo0521201,10.1039/b608410a,10.1016/j.jorganchem.2005.08.035,10.1002/chem.200500231,10.1021/om0501879,10.1055/s-2005-864790,10.1002/chem.200400928,10.1021/ol047670k,10.1021/om049448p,10.1246/cl.2004.1356,10.1002/ejoc.200400258,10.1021/om049786q,10.1021/jo035834p,10.1039/b409241d,10.1039/b408185d,10.1021/om034046n,10.1016/S0022-328X(03)00458-3,10.1016/S0040-4039(03)01789-1,10.1002/adsc.200390036,10.1002/aoc.398,10.1021/ja0286876,10.1039/b306635e,10.1039/b207002m,10.1016/S0040-4039(02)02212-8,10.1016/S0040-4039(02)01502-2,10.1039/b209855e3/10/2022
389
117FALSEom300566m10.1021/om300566mhttps://sci-hub.wf/10.1021/om300566mhttps://doi.org/10.1021/om300566mNiC-O ActivationGerry10-FebTRUE588342012
Belderrain, TR
Nickel(0)/imidazolium chloride catalyzed reduction of aryl halides
ORGANOMETALLICS
Dehalogenation of aryl halides was efficiently performed in refluxing THF using a catalytic combination composed of Ni(0)/N-heterocyclic carbene (NHC)/beta-hydrogen-containing alkoxide. 1Mes.HCl (1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride) and Ni(acac)2 used respectively as carbene and Ni(0) precursors associated to in situ generated i-PrONa were found to be the most effective for the dehalogenation of functionalized aryl chlorides, bromides, iodides, and polyhalogenated hydrocarbons.
Univ Huelva9/10/2012Csp2_ar-Nsp3E-NuOHOTsHAryl
Morpholine
LiOtBuIonic-OtBuWeak0.36_xx10.1021/ol403209k,10.1002/anie.201410875,10.1038/ncomms11073,10.1021/acs.orglett.7b00556,10.1021/acscatal.8b01879,10.1021/acscatal.9b00884,10.1002/anie.201806790,10.1021/acscatal.6b0086510.1002/ejic.202101006,10.1002/tcr.202100204,10.1055/a-1647-5978,10.1039/d1cy00374g,10.1055/s-0040-1707356,10.1021/acs.organomet.9b00672,10.1016/bs.adomc.2020.02.001,10.3390/inorganics7060078,10.1021/acscatal.9b00884,10.1039/c9dt00668k,10.1021/acs.chemrev.8b00505,10.1002/anie.201814233,10.7536/PC180446,10.1021/acs.organomet.8b00394,10.1002/anie.201806790,10.1021/acscatal.8b01879,10.1021/acscatal.8b02187,10.1021/acs.organomet.8b00074,10.1021/acscatal.8b00856,10.1021/acs.orglett.7b03560,10.1021/acscatal.7b03215,10.1021/jacs.7b05574,10.1021/acs.joc.7b01034,10.1039/c7dt01805c,10.1002/chem.201701362,10.1021/acs.organomet.7b00129,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1016/j.jorganchem.2016.12.029,10.1021/acs.organomet.6b00457,10.1021/acs.organomet.6b00473,10.1002/tcr.201500305,10.1021/acs.organomet.6b00415,10.1021/acscatal.6b00865,10.1038/ncomms11073,10.1021/acscatal.5b02021,10.1021/acs.oprd.5b00314,10.1021/jacs.5b08448,10.1002/ejoc.201500734,10.1021/acs.joc.5b01272,10.1021/jacs.5b03587,10.1016/j.ica.2014.11.005,10.1021/ic502792q,10.1002/adsc.201500030,10.1002/anie.201500404,10.1002/anie.201410875,10.1016/j.molcata.2014.10.031,10.1021/om500088p,10.1021/ja411911s,10.1021/ol403209k,10.1039/c4qo00233d,10.1039/c4dt02374a,10.1039/c3dt53352b,10.1021/ja407749wKelly1/10/2022
390
226FALSEnature1467610.1038/nature14676https://sci-hub.wf/10.1038/nature14676https://doi.org/10.1038/nature14676NiC-O ActivationShihongTRUE18011382015Weix, DJ
Synthesis, Structural Characterization, and Catalytic Activity of IPrNi(styrene)(2) in the Amination of Aryl TosylatesNATURE
A novel bis-styrene IPrNi0 derivative has been synthesized from the reaction of Ni(COD)(2) and free 1,3-bis(2,6-diisopropylphenyl)imidazolidene (IPr) ligand in the presence of styrene. The complex has been characterized by spectroscopic data as well as by X-ray crystallography. Its catalytic performance in the amination reaction of aryl tosylates is also reported. The catalytic reactions proceed in a very selective manner, affording moderate to high yields of cross-coupling products in short reaction times at 110 degrees C.
Univ Rochester8/27/2015TRUETRUETRUECsp2_ar-Csp2_arE-EOXOTfBrArylArylNo baseNo BaseWeak0.53_10.1002/anie.201601206,10.1021/jacs.0c04670,10.1021/acscatal.0c03993,10.1021/jacs.7b02326,10.1021/jacs.9b05461,10.1021/acs.orglett.7b00831,10.1021/acs.orglett.6b02656,10.1021/jacs.7b13601,10.1021/jacs.9b05224,10.1039/c7cc06717h,10.1039/c7sc03140h10.1039/d2cp00105e,10.1002/adsc.202101388,10.1021/acscatal.1c04533,10.1021/acs.orglett.1c03991,10.1021/jacs.1c10907,10.1039/d1sc03865f,10.1039/d1qo01406d,10.1021/acscatal.1c04128,10.6023/A21070345,10.1021/acs.orglett.1c03305,10.1039/d1qo01474a,10.1039/d1ob01874d,10.1021/acscatal.1c02307,10.1021/acscatal.1c02952,10.1055/a-1608-5693,10.1021/jacs.1c06271,10.1016/j.chempr.2021.06.007,10.1039/c9cs00571d,10.1021/jacs.1c04215,10.1002/cjoc.202100034,10.1021/acscatal.1c01416,10.1039/d1ob00791b,10.1055/a-1507-4153,10.1021/acs.accounts.1c00096,10.1021/acscatal.1c01102,10.1021/acs.orglett.1c00313,10.1039/d0sc06586b,10.1021/acs.organomet.0c00813,10.1002/chem.202100075,10.1002/chem.202004437,10.1021/acs.joc.0c02722,10.1021/acs.orglett.0c03939,10.1039/d0cy01881c,10.1016/bs.adomc.2021.01.001,10.1021/jacs.0c09922,10.1021/acs.chemrev.0c00245,10.1055/s-0040-1707342,10.1002/jcc.26471,10.1038/s41467-020-19944-x,10.1021/acscatal.0c03993,10.1002/anie.202010631,10.1021/acscatal.0c03903,10.1002/adsc.202000985,10.1002/ijch.202000069,10.1039/d0sc03217d,10.1016/j.chempr.2020.09.004,10.1039/d0qo00615g,10.1021/acs.orglett.0c02165,10.1039/d0sc02054k,10.1002/anie.202005891,10.1002/aoc.5966,10.1021/jacs.0c05730,10.1038/s41467-020-17224-2,10.1021/acs.oprd.0c00134,10.1021/jacs.0c04670,10.1021/jacs.9b13117,10.1177/1934578X20925340,10.1021/jacs.0c00283,10.1021/acscatal.0c00789,10.1021/acs.orglett.0c00199,10.1055/s-0039-1690769,10.1002/ejoc.201901466,10.1002/asia.201901490,10.1039/c9sc04127c,10.1016/j.trechm.2019.08.004,10.1002/chem.201904545,10.1021/acs.orglett.9b02940,10.1021/acs.orglett.9b03147,10.1039/c9gc02464f,10.1016/j.chempr.2019.07.023,10.1021/jacs.9b08504,10.1021/acs.joc.9b01556,10.1039/c9sc02431j,10.1021/jacs.9b05224,10.1002/chem.201900822,10.1021/jacs.9b05461,10.1021/acs.orglett.9b01576,10.1055/s-0037-1612214,10.1002/cctc.201900230,10.1021/acs.orglett.9b01097,10.1021/acs.orglett.9b00692,10.6023/cjoc201806038,10.1126/science.aaw5825,10.1039/c8py01162a,10.1039/c8sc04335c,10.1002/chem.201805682,10.2174/1570179416666191104093533,10.1039/c8qo01044g,10.1021/acscatal.8b03930,10.1038/s41467-018-07198-7,10.1055/s-0037-1610273,10.1002/anie.201805961,10.1021/jacs.8b08190,10.1038/s41557-018-0078-8,10.1021/acscatal.8b02784,10.1055/s-0037-1610161,10.1021/jacs.8b06458,10.1021/acscatal.8b02026,10.1039/c8cc04127j,10.1002/anie.201803603,10.1039/c8ob01034j,10.1002/asia.201701766,10.1021/acscatal.8b00230,10.1039/c8cc00358k,10.1021/acs.orglett.8b00235,10.1039/c8cc00001h,10.1021/jacs.7b13601,10.1021/acs.orglett.8b00114,10.1002/anie.201711990,10.1039/c7cc09675e,10.1007/s11814-017-0281-0,10.1039/c7sc03140h,10.1039/c7ob02895d,10.1021/acs.orglett.7b03482,10.1080/00958972.2018.1439163,10.1039/c7cc06717h,10.1021/acssuschemeng.7b02739,10.1021/acs.organomet.7b00613,10.1002/chem.201702015,10.1002/anie.201706781,10.1021/jacs.7b06469,10.1021/jacs.7b07488,10.1055/s-0036-1588464,10.1039/c7ob01237c,10.1039/c7sc01170a,10.1021/acs.orglett.7b00831,10.1021/jacs.7b02326,10.1039/c6dt04533b,10.1021/acs.joc.7b00010,10.1021/acs.chemrev.6b00731,10.1021/acs.joc.7b00002,10.1039/c6sc05556g,10.1016/j.jorganchem.2016.10.040,10.1039/c6qo00451b,10.1002/anie.201607959,10.1021/acs.orglett.6b02656,10.1002/anie.201607270,10.1002/anie.201608535,10.1007/s11172-016-1619-1,10.1002/ejoc.201601024,10.1021/acs.orglett.6b02862,10.1002/adsc.201600549,10.1038/srep33131,10.1002/ejoc.201600772,10.1021/acs.orglett.6b01837,10.1007/s41061-016-0042-2,10.1021/acs.orglett.6b01420,10.1021/acs.joc.6b00883,10.1002/slct.201600532,10.1002/ejic.201600090,10.1038/ncomms11676,10.1002/anie.201601206,10.1021/acsmacrolett.6b00279,10.1055/s-0035-1561563,10.1002/chem.201505002,10.1021/jacs.6b00016,10.1038/srep19723,10.1021/jacs.5b09223Kelly11/11/2021AUG 272015FALSEFALSEFALSEFALSE5247566454
391
412FALSEc6sc03902b10.1039/c6sc03902bhttps://sci-hub.wf/10.1039/c6sc03902bhttps://doi.org/10.1039/c6sc03902bNiC-N activationGerry2-MarFALSE591#N/A2017Feng, XM#N/AA new approach to the asymmetric Mannich reaction catalyzed by chiral N,N′-dioxide–metal complexesChem. Sci.
A highly efficient asymmetric Mannich-type reaction between α-tetralone-derived β-keto esters/amides and 1,3,5-triaryl-1,3,5-triazinanes was realized in the presence of chiral N,N′-dioxide–Ni(II) or Mg(II) complex. A variety of optically active β-amino compounds with all-carbon quaternary stereocenters were obtained in good yields with excellent enantioselectivities. A possible transition state was proposed based on these experiments and previous reports.
2/1/2017_10.1021/acs.joc.1c02649,10.1039/d1cc06549a,10.1002/ejoc.202101233,10.6023/cjoc202107023,10.1134/S1070428021110014,10.1002/asia.202100833,10.1039/d1qo00748c,10.1039/d1qo00883h,10.1016/j.tet.2021.132130,10.1002/anie.202016220,10.1039/d1cc00093d,10.1002/ajoc.202100098,10.1021/acs.orglett.1c00034,10.24200/sci.2020.54123.3607,10.1002/adsc.202001103,10.1055/s-0040-1707222,10.1021/acs.joc.0c01984,10.1055/s-0040-1707160,10.1002/adsc.202000713,10.1186/s13065-020-00697-z,10.1002/ejoc.202000569,10.1039/d0ra03209c,10.1038/s41467-020-15345-2,10.1002/adsc.201901169,10.1021/acs.orglett.9b03468,10.1039/c9ob01767d,10.1016/j.tet.2019.130571,10.1016/j.jorganchem.2019.06.032,10.1021/acs.joc.9b01959,10.1002/open.201900150,10.1039/c9cc02294e,10.1021/acs.orglett.9b01183,10.1021/acsmedchemlett.9b00019,10.1021/jacs.8b12832,10.1002/adsc.201801063,10.1021/acs.orglett.8b02274,10.1055/s-0037-1610201,10.1039/c8ob01524d,10.1039/c8dt01069b,10.1021/acs.orglett.8b01584,10.1021/acs.orglett.8b00951,10.1002/ajoc.201700679,10.1016/j.reactfunctpolym.2018.01.014,10.1016/j.tetlet.2018.01.016,10.1039/c7ra11973a,10.1039/c7cc07554e,10.1002/anie.201707005,10.1039/c7ob02115a,10.1039/c7sc02576a,10.1002/anie.201704619,10.1002/ejoc.201700463,10.1021/acscatal.7b00787,10.1039/c7cc00789b,10.1021/acs.orglett.7b00600,10.1021/acs.joc.6b02947,10.1021/acs.orglett.6b03691#N/A
392
257FALSEnchem.274110.1038/nchem.2741https://sci-hub.wf/10.1038/nchem.2741https://doi.org/10.1038/nchem.2741NiC-O ActivationGerry1-MarTRUE1314452017Doyle, AG
Multimetallic catalysed cross-coupling of aryl bromides with aryl triflates
NATURE CHEMISTRY
The advent of transition-metal catalysed strategies for forming new carbon-carbon bonds has revolutionized the field of organic chemistry, enabling the efficient synthesis of ligands, materials, and biologically active molecules(1-3). In cases where a single metal fails to promote a selective or efficient transformation, the synergistic cooperation(4) of two distinct catalysts-multimetallic catalysis-can be used instead. Many important reactions rely on multimetallic catalysis(5-10), such as the Wacker oxidation of olefins(6-8) and the Sonogashira coupling of alkynes with aryl halides(9,10), but this approach has largely been limited to the use of metals with distinct reactivities, with only one metal catalyst undergoing oxidative addition(11,12). Here, we demonstrate that cooperativity between two group 10 metal catalysts-(bipyridine)nickel and (1,3-bis(diphenylphosphino) propane) palladiumenables a general cross-Ullmann reaction (the cross-coupling of two different aryl electrophiles)(13-15). Our method couples aryl bromides with aryl triflates directly, eliminating the use of arylmetal reagents and avoiding the challenge of differentiating between multiple carbon-hydrogen bonds that is required for direct arylation methods(16,17). Selectivity can be achieved without an excess of either substrate and originates from the orthogonal reactivity of the two catalysts and the relative stability of the two arylmetal intermediates. While (1,3-bis(diphenylphosphino) propane) palladium reacts preferentially with aryl triflates to afford a persistent intermediate, (bipyridine) nickel reacts preferentially with aryl bromides to form a transient, reactive intermediate. Although each catalyst forms less than 5 per cent cross-coupled product in isolation, together they are able to achieve a yield of up to 94 per cent. Our results reveal a new method for the synthesis of biaryls, heteroaryls, and dienes, as well as a general mechanism for the selective transfer of ligands between two metal catalysts. We anticipate that this reaction will simplify the synthesis of pharmaceuticals, many of which are currently made with pre-formed organometallic reagents(1-3), and lead to the discovery of new multimetallic reactions.
8/1/2017Csp2_ar-Csp2_arE-NuOBOMeB(OH)2ArylArylNo baseNo BaseStrong-0.28_10.1038/s41467-021-25222-1,10.1021/acs.orglett.9b04497,10.1021/jacs.9b00111,10.1021/jacs.7b0238910.1039/d2cp00105e,10.1039/d2sc00174h,10.1063/5.0079574,10.1016/j.chempr.2022.01.005,10.1021/jacs.1c12198,10.1021/acscatal.1c04479,10.1021/acscatal.1c05586,10.1021/acs.orglett.1c04134,10.1021/acs.jpclett.1c04099,10.1021/acscatal.1c04479,10.1002/chem.202103555,10.1021/jacs.1c08399,10.6023/cjoc202106021,10.1126/science.abj4213,10.1021/acs.inorgchem.1c01432,10.1002/tcr.202100210,10.1002/adsc.202100594,10.1038/s42004-021-00550-x,10.1039/d1dt01754c,10.1007/s11172-021-3213-4,10.1021/jacs.1c05281,10.1039/c9cs00571d,10.1039/d1dt01716k,10.1039/d1qo00549a,10.1002/ejic.202100148,10.1002/anie.202103327,10.1016/j.jorganchem.2021.121806,10.1039/d0qo01194k,10.1246/bcsj.20200364,10.1021/acs.accounts.0c00770,10.1021/acs.organomet.0c00775,10.1039/d0cs01107j,10.1039/d0qi01241f,10.1016/j.cclet.2020.04.005,10.1021/acs.accounts.0c00745,10.1021/acs.jcim.0c01041,10.1039/d0sc04074f,10.1021/acs.inorgchem.0c02831,10.1021/acscatal.0c04199,10.1021/acs.orglett.0c03377,10.1021/jacs.0c10832,10.1021/acscatal.0c03939,10.1002/cctc.202001462,10.1016/j.ceramint.2020.05.133,10.1039/d0qo00544d,10.1021/acs.orglett.0c02016,10.1039/d0dt01694b,10.1039/d0gc00763c,10.1021/acs.organomet.9b00834,10.1039/d0sc00445f,10.1002/anie.201915386,10.1016/j.poly.2020.114380,10.1016/j.chempr.2019.12.010,10.1021/acscatal.9b04186,10.1021/acs.organomet.9b00672,10.1021/acs.chemrev.9b00491,10.1021/acs.joc.9b02107,10.1021/acscatal.9b03012,10.1039/c9ob02129a,10.1039/c9dt02876e,10.1038/s41557-019-0319-5,10.1016/j.jorganchem.2019.06.003,10.1002/anie.201906781,10.1002/ejoc.201900850,10.1002/cssc.201900914,10.1021/acs.orglett.9b01669,10.1039/c9cc01977d,10.1002/anie.201902405,10.1021/acs.chemrev.8b00588,10.1039/c9ob00561g,10.1021/jacs.9b02312,10.1021/acs.organomet.9b00027,10.1021/jacs.9b02158,10.1016/j.jcat.2019.04.001,10.1021/acs.orglett.9b00888,10.1021/acs.orglett.9b00294,10.1002/anie.201813278,10.1002/chem.201804805,10.1021/acs.organomet.8b00566,10.1021/acs.organomet.8b00307,10.1021/acs.inorgchem.8b02915,10.1002/chem.201803598,10.1021/acs.organomet.8b00539,10.1021/jacs.8b09103,10.1126/science.aat2299,10.1055/s-0037-1610158,10.1002/cctc.201800629,10.1021/acs.organomet.8b00438,10.1021/acs.orglett.8b02481,10.1038/s41570-018-0040-8,10.1002/anie.201805372,10.1021/acs.inorgchem.8b01565,10.1021/acs.inorgchem.8b01657,10.1002/anie.201804479,10.1021/jacs.8b02469,10.1021/acscatal.8b01005,10.1021/jacs.8b02547,10.1021/jacs.8b01800,10.1039/c7sc04679k,10.1246/cl.171130,10.1021/jacs.7b12212,10.1039/c7sc04604a,10.1021/jacs.7b10855,10.1021/acscatal.7b03079,10.1021/acscatal.7b03432,10.1021/jacs.7b07373,10.1002/anie.201708231,10.1021/jacs.7b09541,10.1002/anie.201706794,10.1002/anie.201706868,10.1021/acscatal.7b02014,10.1039/c7sc02692g,10.1038/nchem.2851,10.1021/acscatal.7b00757,10.1021/acscatal.7b00739Kelly3/9/2022
393
261FALSEncomms1107310.1038/ncomms11073https://sci-hub.wf/10.1038/ncomms11073https://doi.org/10.1038/ncomms11073NiC-O ActivationGerry3-MarTRUE10111382016Stradiotto, M
Parameterization of phosphine ligands demonstrates enhancement of nickel catalysis via remote steric effects
NATURE COMMUNICATIONS
The field of Ni-catalysed cross-coupling has seen rapid recent growth because of the low cost of Ni, its earth abundance, and its ability to promote unique cross-coupling reactions. Whereas advances in the related field of Pd-catalysed cross-coupling have been driven by ligand design, the development of ligands specifically for Ni has received minimal attention. Here, we disclose a class of phosphines that enable the Ni-catalysed Csp(3) Suzuki coupling of acetals with boronic acids to generate benzylic ethers, a reaction that failed with known ligands for Ni and designer phosphines for Pd. Using parameters to quantify phosphine steric and electronic properties together with regression statistical analysis, we identify a model for ligand success. The study suggests that effective phosphines feature remote steric hindrance, a concept that could guide future ligand design tailored to Ni. Our analysis also reveals that two classic descriptors for ligand steric environment-cone angle and % buried volume-are not equivalent, despite their treatment in the literature.
3/1/2016Csp2_ar-Nsp3E-NuOHOTsHAryl
N(Alkyl)Alkyl
Ionic-OtBuWeak0.36_10.1021/acscatal.8b01879,10.1002/anie.201806790,10.1038/NCHEM.2741,10.1021/jacs.8b01800,10.1021/acscatal.7b02014,10.1021/acscatal.1c03010,10.1002/anie.202002392,10.1021/acs.orglett.7b00556,10.1002/chem.201605095,10.1002/anie.202200352,10.1002/anie.20201434010.1002/anie.202200352,10.1021/acscatal.1c04479,10.1021/acscatal.1c05386,10.1021/acscatal.1c05586,10.1021/acscatal.1c04479,10.1021/acscatal.1c05386,10.1016/j.jorganchem.2021.122145,10.1002/cctc.202101013,10.1002/anie.202108587,10.1021/acscatal.1c03010,10.1021/jacs.1c05281,10.1039/d0qo01194k,10.1021/acs.orglett.0c03836,10.1002/anie.202012877,10.1002/anie.202014340,10.1021/acscatal.0c03888,10.1055/a-1337-6459,10.1021/acs.orglett.0c02672,10.1021/acs.chemrev.0c00088,10.1002/chem.202002800,10.1021/jacs.0c06139,10.1055/s-0040-1707356,10.1021/acs.chemrev.9b00682,10.1021/acs.orglett.0c01600,10.1007/s10562-019-03062-5,10.1021/acs.organomet.0c00060,10.1002/chem.201904987,10.1002/anie.202002392,10.1002/ejoc.201901835,10.1021/acscatal.9b03827,10.1021/acs.chemrev.9b00491,10.1002/chem.201903696,10.1002/ejic.201900972,10.1021/acscatal.9b03715,10.1016/j.mcat.2019.110462,10.1002/adsc.201900545,10.1021/acs.orglett.9b01968,10.1039/c9sc00554d,10.1002/anie.201900095,10.1021/jacs.9b01886,10.1021/jacs.9b00931,10.1021/acs.orglett.9b00294,10.1039/c8ob02708k,10.1002/anie.201812862,10.1021/jacs.8b12495,10.1021/acs.organomet.8b00451,10.1080/00958972.2018.1540779,10.1021/acs.organomet.8b00589,10.1021/acs.organomet.8b00605,10.1021/acs.organomet.8b00567,10.1002/anie.201806790,10.1021/acs.joc.8b01205,10.1021/acscatal.8b01879,10.1021/acscatal.8b02187,10.1021/jacs.8b03744,10.1021/acscatal.8b01005,10.1002/anie.201713304,10.1021/acscatal.8b00856,10.1021/jacs.8b02547,10.1021/acs.orglett.8b00646,10.1021/jacs.8b01800,10.1055/s-0036-1591523,10.1002/anie.201800699,10.1021/acs.orglett.7b03560,10.1038/s41929-017-0007-z,10.1021/acscatal.7b03215,10.1002/ajoc.201700464,10.1021/acs.oprd.7b00285,10.1002/anie.201707906,10.1039/c7ob01791j,10.1002/adsc.201700672,10.1021/acscatal.7b02014,10.1002/chem.201702168,10.1055/s-0036-1588806,10.1055/s-0036-1590819,10.1038/NCHEM.2741,10.1021/acs.organomet.7b00373,10.1038/s41570-017-0052,10.1002/ejoc.201700660,10.1039/c7ob00841d,10.1039/c7dt01805c,10.1021/acs.orglett.7b00556,10.1002/adsc.201601105,10.1021/acscatal.6b02988,10.1038/s41570-017-0025,10.1021/acs.organomet.6b00769,10.1021/acs.organomet.6b00885,10.1039/c6sc03699f,10.1021/acs.organomet.6b00830,10.1002/chem.201605095,10.1002/anie.201606979,10.1021/acs.organomet.6b00650,10.1016/j.ica.2016.06.023Kelly3/10/2022
394
150FALSEncomms1487810.1038/ncomms14878https://sci-hub.wf/10.1038/ncomms14878https://doi.org/10.1038/ncomms14878NiC-O ActivationGerryTRUE884722017Hu, XL
Challenging nickel-catalysed amine arylations enabled by tailored ancillary ligand design
NATURE COMMUNICATIONS
Palladium-catalysed C(sp(2))-N cross-coupling (that is, Buchwald-Hartwig amination) is employed widely in synthetic chemistry, including in the pharmaceutical industry, for the synthesis of (hetero) aniline derivatives. However, the cost and relative scarcity of palladium provides motivation for the development of alternative, more Earth-abundant catalysts for such transformations. Here we disclose an operationally simple and air-stable ligand/nickel(II) pre-catalyst that accommodates the broadest combination of C(sp(2))-N coupling partners reported to date for any single nickel catalyst, without the need for a precious-metal co-catalyst. Key to the unprecedented performance of this pre-catalyst is the application of the new, sterically demanding yet electron-poor bisphosphine PAd-DalPhos. Featured are the first reports of nickel-catalysed room temperature reactions involving challenging primary alkylamine and ammonia reaction partners employing an unprecedented scope of electrophiles, including transformations involving sought-after (hetero) aryl mesylates for which no capable catalyst system is known.
Ecole Polytech Fed Lausanne
3/27/2017TRUETRUEFALSEyCsp2-Nsp3E-EOOOMeOH
Carbonyl
N(H)Aryl
No baseNo BaseStrong-0.28_10.1021/acscatal.9b00884,10.1002/anie.201808560,10.1002/chem.201702867,10.1021/acscatal.7b0368810.1002/ejoc.202101505,10.1038/s41467-022-28005-4,10.1021/acs.orglett.1c03535,10.1002/cssc.202101924,10.1021/acs.orglett.1c03343,10.1039/d1qo01269j,10.1021/acscatal.1c03113,10.1002/tcr.202100224,10.1002/anie.202106412,10.1038/s41467-021-24908-w,10.1002/cssc.202101203,10.1002/anie.202104319,10.1002/slct.202101011,10.1039/d0ra10868e,10.6023/cjoc202009048,10.1039/d1gc00720c,10.1246/bcsj.20200277,10.1039/d1cc00047k,10.1021/jasms.0c00384,10.1016/j.tetlet.2020.152801,10.1002/adsc.202001496,10.1039/d0gc03912h,10.1002/anie.202012877,10.1021/acs.joc.0c02478,10.1021/acs.orglett.0c03666,10.7536/PC200607,10.1002/pep2.24210,10.1016/j.saa.2020.118667,10.1021/acscatal.0c03334,10.1055/s-0040-1707101,10.1002/adsc.202000370,10.1002/cplu.202000451,10.1016/S1872-2067(20)63561-6,10.1021/acs.oprd.0c00134,10.1021/jacs.0c01666,10.3390/molecules25051040,10.1021/acscatal.9b05049,10.1039/c9cy02080b,10.1002/anie.201914851,10.1039/c9ra10758d,10.1021/acscatal.9b03894,10.2174/1574893615666200129110450,10.2174/1570179417666200212113412,10.24820/ark.5550190.p011.417,10.1021/acs.orglett.9b04092,10.1039/c9cc06638a,10.1021/acs.joc.9b02068,10.1039/c9ra06724h,10.1039/c9na00368a,10.1021/acs.orglett.9b01849,10.1021/acs.joc.9b01113,10.1021/jacs.9b04136,10.1002/anie.201814197,10.1021/acscatal.9b00884,10.1039/c9ob00699k,10.1039/c8qo01405a,10.1021/acs.orglett.9b00554,10.1021/acs.orglett.9b00191,10.1002/anie.201812806,10.1055/s-0037-1610664,10.1039/c8ob02539h,10.1002/anie.201808560,10.1021/acs.orglett.8b02109,10.1039/c8nj02413h,10.1016/j.chempr.2018.04.008,10.1021/jacs.8b03739,10.1021/acs.orglett.8b01305,10.1021/acscatal.7b03688,10.1039/c7sc03950f,10.1021/acs.orglett.7b03669,10.1002/anie.201709180,10.1021/acscatal.7b02859,10.1002/anie.201705356,10.1002/chem.201702867Kelly1/14/2022MAR 272017FALSEFALSEFALSEFALSE8
395
283FALSEs41467-018-07198-710.1038/s41467-018-07198-7https://sci-hub.wf/10.1038/s41467-018-07198-7https://doi.org/10.1038/s41467-018-07198-7NiC-O ActivationLong14-AprTRUE36422018Li, C
Direct amidation of esters with nitroarenes
NATURE COMMUNICATIONS
Esters are one of the most common functional groups in natural and synthetic products, and the one-step conversion of the ester group into other functional groups is an attractive strategy in organic synthesis. Direct amidation of esters is particularly appealing due to the omnipresence of the amide moiety in biomolecules, fine chemicals, and drug candidates. However, efficient methods for direct amidation of unactivated esters are still lacking. Here we report nickel-catalysed reductive coupling of unactivated esters with nitroarenes to furnish in one step a wide range of amides bearing functional groups relevant to the development of drugs and agrochemicals. The method has been used to expedite the syntheses of bio-active molecules and natural products, as well as their post-synthetic modifications. Preliminary mechanistic study indicates a reaction pathway distinct from conventional amidation methods using anilines as nitrogen sources. The work provides a novel and efficient method for amide synthesis.
11/9/2018Csp2_ar-Csp2_arE-EOOOTfOTfArylArylK3PO4Ionic-PO4Weak0.5310.1021/jacs.1c10932,10.1021/jacs.0c04670,10.1021/acscatal.0c03993,10.1021/jacs.0c0699510.1007/s10904-022-02340-x,10.1039/d2ra00010e,10.1021/jacs.1c10907,10.1021/jacs.1c10932,10.1039/d1qo01406d,10.1021/acscatal.1c02952,10.1038/s41467-021-23971-7,10.1055/a-1509-5954,10.1055/a-1503-6330,10.1021/acscatal.1c01102,10.1039/d0sc06586b,10.1016/j.molliq.2020.115174,10.1021/acscatal.0c03993,10.1021/acscatal.0c03237,10.1002/ijch.202000069,10.1002/ajoc.202000242,10.1021/jacs.0c06995,10.1016/j.isci.2020.101419,10.1126/science.aba3823,10.1021/jacs.0c04670,10.1016/j.jcat.2020.02.021,10.1021/acs.orglett.0c00199,10.1002/anie.201915218,10.1039/c9sc03737c,10.1002/asia.201901490,10.1039/c9cc06127d,10.1021/acscatal.9b02483,10.1055/s-0037-1611853,10.1007/s12039-019-1638-1,10.1038/s41467-019-08631-1#REF!
396
286FALSEs41467-020-17224-210.1038/s41467-020-17224-2https://sci-hub.wf/10.1038/s41467-020-17224-2https://doi.org/10.1038/s41467-020-17224-2NiC-O ActivationxJustin28-MayTRUE391#N/A2020Xie, J
N2H4 as traceless mediator for homo- and cross-aryl coupling
NATURE COMMUNICATIONS
Transition-metal catalyzed couplings of aryl halides or arenes with aryl organometallics, as well as direct reductive coupling of two aryl halides, are the predominant methods to synthesize biaryls. However, stoichiometric amounts of metals are inevitably utilized in these reactions, either in the pre-generation of organometallic reagents or acting as reductant in situ, thus producing quantitative metal waste. Herein, we demonstrate that this long-standing challenge can be overcome with N2H4 as a metal surrogate. The fundamental innovation of this strategy is that N-2 and H-2 are generated as side products, which readily escape from the system after the reaction. The success of both homo- and cross-coupling of various aryl electrophiles bearing a wide range of functional groups manifests the powerfulness and versatility of this strategy. Furthermore, both homo- and cross-couplings of a series of alkaloids, amino acids and steroids exemplify application of this protocol in the functionalization of biologically active molecules.
7/3/2020Csp2-Csp2_arE-EOXOHBr
Carbonyl
ArylNo baseNo BaseStrong-0.816/15/2022
397
418FALSEacs.organomet.9b0066810.1021/acs.organomet.9b00668https://sci-hub.wf/10.1021/acs.organomet.9b00668https://doi.org/10.1021/acs.organomet.9b00668NiC-H ActivationGerry5-MarTRUE41#N/A2019
12/9/2019Csp2_ar-Csp2_arNu-NuHHHHHetHetNo baseNo BaseNu-H_10.1038/s41467-020-20725-910.1016/j.poly.2021.115357,10.1002/adsc.202001498,10.1021/acs.organomet.0c003553/10/2022
398
419FALSEnature2281310.1038/nature22813https://sci-hub.wf/10.1038/nature22813https://doi.org/10.1038/nature22813NiC-H ActivationxGerry7-MarTRUE2832#N/A2017
7/6/2017Csp3-Csp3E-NuHXHBrAlkylAlkylIonic-CO3Nu-H_10.1021/acscatal.9b00521,10.1021/acs.orglett.9b0101610.1055/a-1677-6619,10.1007/s10562-022-03936-1,10.1002/cssc.202102317,10.1039/d1qo01871j,10.1021/acscatal.1c05484,10.1039/d1sc07067c,10.1039/d1cc06885g,10.1021/jacs.1c09412,10.1039/d1sc06784b,10.3762/bjoc.17.205,10.1021/acs.inorgchem.1c02118,10.1021/acs.orglett.1c04088,10.1039/d1cc06285a,10.1038/s41467-021-27165-z,10.1002/anie.202114490,10.1021/acscatal.1c04142,10.1002/anie.202110583,10.1039/d1dt03353k,10.1002/anie.202109849,10.1021/acscatal.1c04314,10.1002/anie.202107253,10.1002/ajoc.202100467,10.1021/acs.joc.1c01881,10.1021/jacs.1c05479,10.1002/wcms.1573,10.1021/jacs.1c07401,10.1039/d1qo01325d,10.1038/s41467-021-25594-4,10.1039/d1sc03563k,10.3762/bjoc.17.143,10.1016/j.mcat.2021.111785,10.1021/jacs.1c05890,10.1039/d1cs00311a,10.1021/acs.orglett.1c02151,10.1021/jacs.1c05498,10.1038/s41570-021-00300-6,10.1039/d1gc01563j,10.1021/acs.orglett.1c01716,10.1021/acs.joc.1c00726,10.1038/s41467-021-23887-2,10.1039/d1cc01756j,10.1016/j.cclet.2021.02.009,10.1021/acscatal.1c01222,10.1039/d1sc00828e,10.1002/cptc.202100059,10.1021/acs.orglett.1c01232,10.1039/d0cs00973c,10.1002/chem.202100902,10.6023/cjoc202009044,10.1021/acs.orglett.1c00831,10.1002/chem.202100902,10.1039/d1sc00161b,10.1039/d0sc05883a,10.1021/jacs.1c01556,10.1039/d0cs01107j,10.1021/acs.joc.1c00188,10.1021/acscatal.0c05725,10.1021/acs.orglett.1c00546,10.1016/j.tetlet.2021.152878,10.1021/jacs.0c13077,10.1021/acscatal.0c05681,10.1021/jacs.1c00288,10.6023/cjoc202005055,10.1016/j.tet.2021.131946,10.1021/acs.orglett.1c00135,10.1021/jacs.1c00687,10.1016/j.tet.2020.131896,10.1021/jacs.1c00549,10.1021/jacs.0c13200,10.1039/d0cs00493f,10.1039/d0ob02417a,10.1021/acs.orglett.0c03992,10.1021/acs.orglett.0c03853,10.1021/acs.orglett.0c03944,10.1002/anie.202013020,10.1039/d0cs00344a,10.1021/acscatal.0c04696,10.21577/0100-4042.20170674,10.1021/acscatal.0c04722,10.1021/acs.joc.0c02227,10.1055/a-1344-2434,10.1021/jacs.0c10616,10.1002/chem.202003541,10.6023/cjoc202006079,10.1007/s10593-020-02823-0,10.1021/jacs.0c10471,10.1021/acs.orglett.0c02902,10.1021/acscatal.0c03851,10.1002/adsc.202000772,10.2533/chimia.2020.895,10.3390/molecules25225270,10.1246/bcsj.20200182,10.1002/anie.202010839,10.6023/A20070335,10.1021/jacs.0c05010,10.1039/d0cs00229a,10.1039/d0nj03733h,10.1021/acscatal.0c02584,10.1021/acscatal.0c03089,10.1021/jacs.0c06997,10.1002/cssc.202001974,10.1039/d0ra07638d,10.3762/bjoc.16.183,10.1021/jacs.0c06882,10.3390/catal10090982,10.1039/d0qo00473a,10.1021/acs.orglett.0c01924,10.1039/d0sc00031k,10.1055/s-0040-1707114,10.1055/s-0040-1707947,10.3762/bjoc.16.147,10.1021/jacs.0c03758,10.1016/j.chempr.2020.04.022,10.1021/acs.chemrev.9b00682,10.1002/anie.202005294,10.1039/d0gc01035a,10.1021/acs.orglett.0c01297,10.1038/s41557-020-0475-7,10.1002/slct.202000947,10.1002/anie.202004272,10.1002/anie.202000743,10.1055/s-0039-1690839,10.1002/adsc.202000167,10.1021/acscatal.0c01318,10.1039/d0sc00964d,10.1021/jacs.0c00212,10.1002/chem.201905773,10.1038/s41467-020-15167-2,10.1038/s41586-020-2137-8,10.1002/ejoc.201901146,10.1021/acs.chemrev.9b00462,10.1021/acscatal.9b04000,10.1039/c9cc09654j,10.1021/acs.orglett.0c00199,10.1021/acscatal.9b04491,10.2533/chimia.2020.23,10.1039/c9sc05132e,10.1039/c9ob01559k,10.1039/c9cc09164e,10.1055/s-0039-1690714,10.1002/anie.201903726,10.1039/c9sc04987h,10.1039/c9cc06985b,10.1002/adsc.201901253,10.6023/cjoc201904022,10.1021/acs.orglett.9b03338,10.1002/cjoc.201900360,10.1038/s41586-019-1655-8,10.1002/ajoc.201900427,10.3390/molecules24173086,10.1002/cctc.201900398,10.1021/jacs.9b06834,10.1021/acs.orglett.9b02226,10.1080/17460441.2019.1653850,10.1002/ejoc.201900868,10.1002/anie.201904707,10.1021/acs.orglett.9b02307,10.1021/jacs.9b05360,10.1002/adsc.201900532,10.1002/ejoc.201900786,10.1055/s-0037-1611852,10.1002/ajoc.201900229,10.1021/acs.joc.9b01163,10.1021/acs.orglett.9b01329,10.1021/acs.orglett.9b01491,10.1021/acs.joc.9b00708,10.1002/asia.201900176,10.1021/acscatal.9b01394,10.1021/acs.joc.9b00237,10.1021/acs.joc.9b00335,10.1021/acs.joc.9b00649,10.1039/c9cc01047e,10.1016/j.tetlet.2019.04.016,10.1002/anie.201809431,10.1021/acs.orglett.9b00442,10.1021/acs.orglett.9b01097,10.1016/j.tetlet.2019.04.017,10.1021/acs.orglett.9b00985,10.1021/jacs.9b01531,10.1055/s-0037-1612079,10.1126/science.aav3200,10.1039/c8sc05677c,10.1039/c8sc05164j,10.1002/anie.201812227,10.1002/anie.201810556,10.1039/c8sc04789h,10.1021/acs.chemrev.8b00507,10.1021/acs.orglett.8b03959,10.1002/anie.201810526,10.1039/c8ob02938e,10.1016/bs.apoc.2019.07.002,10.1080/00397911.2019.1574350,10.1002/adsc.201800736,10.1021/acs.orglett.8b03340,10.1002/ejoc.201800896,10.1039/c8sc02965b,10.1002/anie.201809400,10.1039/c8cc06445h,10.1016/j.chempr.2018.10.014,10.1073/pnas.1806399115,10.1002/cmdc.201800492,10.1039/c8qo00893k,10.1016/j.chempr.2018.09.014,10.1021/jacs.8b08052,10.1021/acs.orglett.8b00991,10.1021/acscatal.8b03031,10.1038/s41557-018-0085-9,10.1021/jacs.8b07405,10.1021/jacs.8b07534,10.1021/acs.accounts.8b00231,10.1055/s-0037-1610222,10.1039/c8sc02253d,10.1126/science.aat9750,10.1016/j.scib.2018.06.004,10.1002/anie.201805927,10.1002/asia.201800584,10.1038/s41586-018-0366-x,10.1021/acscatal.8b00601,10.1021/jacs.8b05753,10.1021/jacs.8b04890,10.1021/jacs.8b05962,10.1002/chem.201801886,10.1007/s10593-018-2330-y,10.1126/sciadv.aat6031,10.1055/s-0037-1609847,10.1021/acs.orglett.8b01382,10.1039/c8cc03550d,10.1039/c8sc01561a,10.1002/chem.201801746,10.1016/j.tetlet.2018.05.008,10.1039/c8qo00098k,10.1021/acs.joc.8b00562,10.1039/c8nj00476e,10.1002/anie.201800749,10.1021/acs.orglett.8b00583,10.1039/c7cc09457d,10.1002/anie.201712731,10.1038/s41557-018-0021-z,10.1021/jacs.8b00592,10.1002/adsc.201701548,10.1002/anie.201712668,10.1021/acs.joc.8b00469,10.1002/anie.201711467,10.1021/acscatal.7b03024,10.1038/nature25185,10.1002/adsc.201701051,10.1088/1361-6528/aa98ee,10.1021/acscatal.7b03354,10.1002/anie.201711250,10.1039/c6cs00787b,10.1126/science.aap9674,10.1039/c7gc02775c,10.1021/acs.joc.7b02134,10.1039/c7sc03613b,10.1021/acscatal.7b02151,10.1021/jacs.7b07078,10.1016/j.chempr.2017.07.014,10.1021/acs.orglett.7b015523/10/2022
399
420FALSEchem.20140645710.1002/chem.201406457https://sci-hub.wf/10.1002/chem.201406457https://doi.org/10.1002/chem.201406457NiC-H ActivationGerry7-MarTRUE313#N/A2015
3/2/2015Csp3-Csp2_arE-NuHXHClAlkylArylIonic-OtBuNu-H_10.1039/c6ob01299j,10.1039/c5sc01589h,10.1002/anie.20200682610.1016/j.tetlet.2021.153208,10.1039/d1cc00913c,10.1039/d0qi01411g,10.1002/anie.202006826,10.1016/j.trechm.2020.06.001,10.1039/d0sc02629h,10.1016/j.tetlet.2020.152124,10.1021/acs.orglett.9b02793,10.1021/acs.orglett.9b02830,10.1021/acs.joc.9b01293,10.3390/inorganics7060078,10.1021/acs.joc.9b00669,10.1021/acs.organomet.8b00589,10.1055/s-0037-1609963,10.1021/acs.inorgchem.7b02097,10.1039/c7dt01912b,10.1002/slct.201701609,10.1002/ejic.201700397,10.1021/acs.organomet.7b00109,10.1002/chem.201700680,10.1038/s41570-017-0025,10.1021/acscatal.6b00040,10.1016/j.jorganchem.2016.02.005,10.1002/anie.201600248,10.1002/chem.201504844,10.1039/c6ob01299j,10.1002/chem.201500834,10.1055/s-0034-1380813,10.1039/c5sc01589h3/10/2022
400
16FALSEs41467-020-20725-910.1038/s41467-020-20725-9https://sci-hub.wf/10.1038/s41467-020-20725-9https://doi.org/10.1038/s41467-020-20725-9NiC-O ActivationGerryTRUE9182021Yu, WY
Upgrading ketone synthesis direct from carboxylic acids and organohalides
NATURE COMMUNICATIONS
The ketone functional group has a unique reactivity in organic chemistry and is associated with a number of useful reactions. Catalytic methods for ketone synthesis are continually being developed. Here, we report a photoredox, nickel and phosphoranyl radical synergistic cross-electrophile coupling of commercially available chemicals, aromatic acids and aryl/alkyl bromides. This allows for concise synthesis of highly functionalized ketones directly, without the preparation of activated carbonyl intermediates or organometallic compounds, and thus complements the conventional Weinreb ketone synthesis. Use of the appropriate photocatalyst, ligand amount and solvents can match the reaction rate required by any simple catalytic cycle. The practicality and synthetic robustness of the reaction are illustrated by the facile synthesis of complex ketones from readily available feedstock chemicals. Due to their abundance and importance in organic chemistry, development of methods for ketone synthesis is essential. Here, the authors report a photoredox, nickel and phosphoranyl radical synergistic cross-electrophile coupling of aromatic acids and aryl/alkyl bromides to directly synthesise ketones.
Hong Kong Polytech Univ
1/18/2021TRUETRUETRUEyyCsp2-Csp2_arE-NuOBOCOPhB(OH)2VinylArylIonic-CO3Strong0.13_x10.1002/chem.202200280,10.1002/adsc.202101388,10.6023/cjoc202108006,10.1021/acs.joc.1c02659,10.1246/bcsj.20210248,10.1021/acs.joc.1c01724,10.1039/d1cc02696h,10.1021/acs.joc.1c005701/14/2022JAN 182021FALSEFALSEFALSEFALSE121
401
293FALSEs41467-021-23887-210.1038/s41467-021-23887-2https://sci-hub.wf/10.1038/s41467-021-23887-2https://doi.org/10.1038/s41467-021-23887-2NiC-O ActivationxLong3-JunTRUE151#N/A2021Huo, HH
2,2-difluorovinyl benzoates for diverse synthesis of gem-difluoroenol ethers by Ni-catalyzed cross-coupling reactions
NATURE COMMUNICATIONS
gem-Difluoroalkene is a bioisostere of carbonyl group for improving bioavailability of drug candidates. Herein we develop structurally diverse 2,2-difluorovinyl benzoates (BzO-DFs) as versatile building blocks for modular synthesis of gem-difluoroenol ethers (44 examples) and gem-difluoroalkenes (2 examples) by Ni-catalyzed cross coupling reactions. Diverse BzO-DFs derivatives bearing sensitive functional groups (e.g., C=C, TMS, strained carbocycles) are readily prepared from their bromodifluoroacetates and bromodifluoroketones precursors using metallic zinc as reductant. With Ni(COD)(2) and dppf [1,1'-bis(diphenylphosphino)ferrocene] as catalyst, reactions of BzO-DFs with arylboronic acids and arylmagnesium/alkylzinc reagents afforded the desired gem-difluoroenol ethers and gem-difluoroalkenes in good yields. The Ni-catalyzed coupling reactions features highly regioselective C(vinyl)-O(benzoate) bond activation of the BzO-DFs. Results from control experiments and DFT calculations are consistent with a mechanism involving initial oxidative addition of the BzO-DFs by the Ni(0) complex. By virtue of diversity of the BzO-DFs and excellent functional group tolerance, this method is amenable to late-stage functionalization of multifunctionalized bioactive molecules. The gem-difluoroalkene functionality is relevant to drug design as it is a bioisostere of a carbonyl group. Here, the authors report the synthesis of 2,2-difluorovinyl benzoates as versatile building blocks for modular synthesis of gem-difluoroenol ethers and gem-difluoroalkenes by nickel-catalyzed cross coupling.
6/10/2022Csp2-Csp2_arE-NuOHOHH
Carbonyl
ArylNo baseNo BaseStrong-0.816/21/2022
402
423FALSEanie.20110835010.1002/anie.201108350https://sci-hub.wf/10.1002/anie.201108350https://doi.org/10.1002/anie.201108350NiC-H ActivationLong8-MarTRUE1583#N/A2012
3/1/2012Csp2-Csp3E-NuHMgHMgXVinylAlkylIonic-PO4Nu-H_10.1002/anie.201307069,10.1021/ja5026485,10.1002/anie.20181075710.1021/acscatal.1c04705,10.1021/acscatal.1c04705,10.1021/acscatal.1c05530,10.1002/adsc.202101015,10.1021/acscatal.1c03009,10.1039/d1ob01405f,10.6023/cjoc202103029,10.1055/a-1516-8481,10.1002/adsc.202100260,10.1039/d0cs01107j,10.1021/acs.joc.0c02277,10.1021/acscatal.0c03621,10.1039/d0cc01217c,10.1002/adsc.202000820,10.1039/d0nj03733h,10.1039/d0qo00671h,10.1002/anie.202000860,10.1039/d0sc01084g,10.1021/acs.orglett.0c00963,10.1021/acs.orglett.0c00561,10.1002/chem.202000114,10.1039/c9ob02289a,10.1002/open.201900220,10.1021/acs.orglett.9b03189,10.1039/c9sc02806d,10.1039/c9gc02725d,10.1038/s42004-019-0219-z,10.1002/tcr.201900053,10.1021/acs.orglett.9b02838,10.6023/A19040121,10.1246/bcsj.20190120,10.1016/j.tetlet.2019.06.005,10.1246/cl.190247,10.1021/acs.joc.9b00898,10.1002/adsc.201801707,10.1002/chem.201406163,10.1002/chem.201805351,10.1021/acs.orglett.9b00600,10.1016/j.tet.2019.03.048,10.1016/j.tetlet.2019.03.002,10.1021/acs.accounts.9b00044,10.1002/anie.201813184,10.1021/acs.orglett.9b00142,10.1021/acscatal.8b04872,10.1055/s-0037-1611659,10.1002/anie.201813689,10.1002/asia.201801732,10.1038/s41467-019-08631-1,10.1021/acs.orglett.8b04024,10.1002/anie.201810757,10.1021/jacs.8b10874,10.1080/00958972.2018.1540779,10.1002/ajoc.201800535,10.1039/c8qo00927a,10.1021/acs.joc.8b02279,10.1039/c8ob01870g,10.1039/c8qo00615f,10.1002/asia.201800630,10.1002/asia.201800534,10.1021/acs.orglett.8b01962,10.1021/acsomega.8b01397,10.1021/acs.orglett.8b01600,10.1021/jacs.8b03163,10.1021/acs.orglett.8b01268,10.1016/j.isci.2018.04.020,10.1021/acs.orglett.8b00221,10.1021/acs.joc.8b00016,10.1002/asia.201701655,10.1039/c7sc04351a,10.1039/c7qo00579b,10.1021/acs.orglett.7b03591,10.1055/s-0036-1590895,10.1021/acs.orglett.7b03289,10.1021/acs.orglett.7b02848,10.1021/jacs.7b06340,10.1002/adsc.201700365,10.1055/s-0036-1588781,10.1021/acs.orglett.7b01020,10.1039/c7cc01790a,10.1039/c6sc05622a,10.1039/c7cc00483d,10.1021/acscatal.6b03287,10.1039/c7ob00009j,10.1055/s-0036-1588642,10.1002/cjoc.201600749,10.1039/c6sc04274k,10.1039/c6cc08392g,10.1039/c7ra07306b,10.1080/00397911.2017.1365905,10.1007/s10562-016-1880-9,10.1021/acs.inorgchem.6b01540,10.1002/chem.201602939,10.1002/anie.201601296,10.1021/jacs.6b02565,10.1002/chem.201600219,10.1002/adsc.201501134,10.1002/anie.201511321,10.1002/anie.201511624,10.1021/acs.orglett.5b03608,10.1039/c6sc01457g,10.1039/c5cc10653b,10.1039/c6ra01918h,10.1039/c5cy02235e,10.1039/c5cc10132h,10.5059/yukigoseikyokaishi.74.2,10.1002/ajoc.201500388,10.1021/acs.orglett.5b02482,10.1021/acs.orglett.5b01662,10.1016/j.tetlet.2015.05.055,10.1002/ajoc.201500148,10.1002/chem.201500560,10.1021/acs.orglett.5b00912,10.1002/anie.201412026,10.1016/j.tet.2015.02.067,10.1055/s-0034-1379939,10.1039/c4cs00347k,10.1002/anie.201410176,10.1002/anie.201410279,10.1039/c5cy00876j,10.1039/c5cc04697a,10.1039/c5cc02254a,10.1002/asia.201403097,10.1039/c5ob00515a,10.1002/chem.201404463,10.1021/ar5002044,10.1002/chem.201404607,10.1021/ol502953w,10.1021/ol502207z,10.1021/ja5066015,10.1002/adsc.201400548,10.1021/ol5014153,10.1021/ja5026485,10.1002/anie.201311323,10.1002/anie.201402893,10.1021/om5001327,10.1002/chem.201304715,10.1515/pac-2014-5034,10.1002/anie.201309134,10.1039/c4sc00093e,10.1039/c4cc00644e,10.1039/c4cc00867g,10.1039/c4cc00297k,10.1039/c4ra08517e,10.1021/ol403021p,10.1002/anie.201307069,10.1021/ja409661n,10.1002/anie.201305885,10.1002/chem.201203694,10.1002/chem.201202950,10.1039/c3cc43875a,10.1039/c3cc42307g,10.1002/anie.201208920,10.1039/c3cc00029j,10.1021/ol3028913,10.1039/c2cc33203e3/10/2022
403
424FALSEs0040-4020(01)89366-210.1016/s0040-4020(01)89366-2https://sci-hub.wf/10.1016/s0040-4020(01)89366-2https://doi.org/10.1016/s0040-4020(01)89366-2NiDeletedLong8-MarFALSE15311061994HAYASHI, T#N/A4/11/1994_10.1021/acs.joc.1c01561,10.1021/acs.orglett.1c02852,10.1055/a-1337-5153,10.1039/c8ob03048k,10.2174/1570179416666190415110834,10.1021/acs.orglett.8b01886,10.1021/acs.orglett.8b00974,10.1039/c8dt00441b,10.1055/s-0036-1590903,10.1002/ejoc.201700239,10.1002/chem.201605712,10.1055/s-0036-1588328,10.1016/j.ccr.2016.09.011,10.1021/jacs.6b09580,10.1002/tcr.201600078,10.1016/j.tet.2015.12.051,10.1002/tcr.201500242,10.1039/c6ob01102k,10.1002/ejoc.201500962,10.1021/acs.organomet.5b00351,10.1002/anie.201500201,10.1021/acs.orglett.5b00844,10.3762/bjoc.10.215,10.1021/cs500208n,10.1002/asia.201301265,10.1080/00304948.2014.922376,10.2174/15701794113109990066,10.1021/ol402666p,10.1021/jo400349r,10.1016/j.apcata.2013.03.027,10.3390/molecules18032788,10.1039/c3cs60116a,10.1055/s-0032-1316825,10.1021/om2008309,10.1002/chem.201100205,10.1002/ejoc.201001242,10.1002/anie.201101147,10.1055/s-0030-1257960,10.1021/ol100697a,10.1016/j.tetasy.2010.05.025,10.1002/ejoc.200901080,10.1515/znb-2009-11-1226,10.1016/j.jorganchem.2008.08.008,10.1002/anie.200900013,10.1246/bcsj.81.1183,10.1002/adsc.200800446,10.1016/j.molcata.2008.01.001,10.1071/CH08095,10.1080/00397910701831498,10.1016/j.tet.2007.06.043,10.1002/adsc.200700155,10.1016/j.tetasy.2007.05.026,10.1021/ja0703170,10.1002/chem.200600993,10.1080/00397910601039044,10.1021/ja063934h,10.2174/138527206778249847,10.1021/jo060945k,10.1002/adsc.200606146,10.1016/j.tetasy.2006.06.013,10.1021/ol060666j,10.1002/anie.200602143,10.1007/s10563-005-9161-4,10.2174/138527205774913097,10.1021/jo051581j,10.1021/jo051283m,10.2174/157017905774322631,10.1016/j.tet.2004.07.093,10.1021/jo049385k,10.1016/j.tetlet.2004.05.101,10.1021/jo035880p,10.1021/om034381b,10.1016/j.tet.2003.12.070,10.5059/yukigoseikyokaishi.62.314,10.1246/bcsj.77.347,10.1016/j.tetasy.2003.10.034,10.1016/j.tetlet.2003.10.176,10.1021/cr9900230,10.1021/ja035293l,10.1246/bcsj.76.1233,10.1016/S0957-4166(03)00088-0,10.1021/ol027256p,10.1021/jo020438c,10.1021/jo0257804,10.1023/A:1022685801622,10.1016/S0040-4020(02)00857-8,10.5059/yukigoseikyokaishi.60.434,10.1002/1521-3749(200206)628:5<971::AID-ZAAC971>3.0.CO;2-G,10.1021/ol025563p,10.1016/S0957-4166(02)00094-0,10.1016/S0040-4020(02)00076-5,10.1021/ja011122+,10.1021/om0108088,10.1039/b107736h,10.1021/jo010691x,10.1016/S0040-4020(01)00087-4,10.1021/jo001614p,10.1246/cl.2000.1272,10.1016/S0920-5861(00)00404-1,10.1016/S0040-4039(00)01276-4,10.3987/COM-00-8920,10.1021/om991013s,10.1021/ar990080f,10.1139/cjc-78-6-697,10.1021/ja9944599,10.1016/S0040-4020(99)01107-2,10.1021/ja994059l,10.1021/jo9916986,10.1021/ja9927220,10.1055/s-1999-3435,10.1021/om980920e,10.1016/S0022-328X(98)01058-4,10.1016/S0040-4020(98)01154-5,10.1002/(SICI)1521-3773(19990816)38:16<2395::AID-ANIE2395>3.3.CO;2-N,10.1023/A:1019075719151,10.1021/jo980757x,10.1021/ja980787h,10.1016/S0040-4039(98)00768-0,10.1039/a801674g,10.5059/yukigoseikyokaishi.56.511,10.1248/yakushi1947.118.6_193,10.1016/S0957-4166(98)00136-0,10.1016/S0040-4039(98)00414-6,10.1021/ja973150r,10.1039/a700045f,10.1016/S0022-328X(96)06712-5,10.1002/anie.199705181,10.1016/0040-4039(96)01718-2,10.1016/0040-4039(96)00786-1,10.1007/BF00817258,10.1002/chem.19960020511,10.3891/acta.chem.scand.50-0259,10.1016/0010-8545(95)00000-3,10.1016/1381-1169(95)00130-1,10.1039/c39950001533,10.1016/0957-4166(95)00053-R,10.1246/bcsj.68.713,10.5059/yukigoseikyokaishi.52.900#N/A
404
292FALSEs41467-021-27507-x10.1038/s41467-021-27507-xhttps://sci-hub.wf/10.1038/s41467-021-27507-xhttps://doi.org/10.1038/s41467-021-27507-xNiC-O ActivationxJustin1-JunTRUE71#N/A2022Xie, J
Asymmetric benzylic C(sp(3))-H acylation via dual nickel and photoredox catalysis
NATURE COMMUNICATIONS
Asymmetric C(sp(3))-H functionalization is a persistent challenge in organic synthesis. Here, we report an asymmetric benzylic C-H acylation of alkylarenes employing carboxylic acids as acyl surrogates for the synthesis of alpha -aryl ketones via nickel and photoredox dual catalysis. This mild yet straightforward protocol transforms a diverse array of feedstock carboxylic acids and simple alkyl benzenes into highly valuable alpha -aryl ketones with high enantioselectivities. The utility of this method is showcased in the gram-scale synthesis and late-stage modification of medicinally relevant molecules. Mechanistic studies suggest a photocatalytically generated bromine radical can perform benzylic C-H cleavage to activate alkylarenes as nucleophilic coupling partners which can then engage in a nickel-catalyzed asymmetric acyl cross-coupling reaction. This bromine-radical-mediated C-H activation strategy can be also applied to the enantioselective coupling of alkylarenes with chloroformate for the synthesis of chiral alpha -aryl esters. Chiral alpha -aryl ketones are versatile building blocks, and represent important pharmacophores existing in many drug molecules such as ibuprofen and naproxen. Here the authors for such ketones but using nickel and photoredox dual catalysis in asymmetric benzylic C-H acylation of alkylarenes and employing carboxylic acids as acyl surrogates.
2/4/2022Csp2_ar-Csp2_arE-EOOOTfOHArylArylNa2CO3Ionic-CO3Weak0.536/15/2022
405
426FALSEanie.20130706910.1002/anie.201307069https://sci-hub.wf/10.1002/anie.201307069https://doi.org/10.1002/anie.201307069NiC-H ActivationLong9-MarTRUE1045#N/A2013
11/18/2013Csp1-Csp3E-NuHXHBrAlkyneAlkylNo baseNo BaseNu-H_10.1021/cs501502u,10.1021/acs.joc.5b00669,10.1021/acs.organomet.6b00529,10.1038/s41467-021-25222-1,10.1039/c7cc01932g10.1055/a-1750-8314,10.1007/s10562-021-03882-4,10.3390/molecules27010033,10.1039/d1nj04485k,10.1039/d1gc03388c,10.1039/d1qo01217g,10.1002/anie.202109723,10.1016/j.jcat.2021.07.023,10.1038/s41467-021-25222-1,10.1039/d1ob00280e,10.1021/acs.organomet.0c00793,10.1002/anie.202100641,10.1016/j.jorganchem.2021.121754,10.1002/adsc.202001325,10.1246/bcsj.20200321,10.1021/acs.chemrev.0c00245,10.1016/j.inoche.2020.108274,10.1021/jacs.0c08652,10.1021/acs.joc.0c01177,10.1002/anie.202000860,10.1021/acs.joc.0c00141,10.1002/adsc.202000189,10.1021/acschemneuro.0c00032,10.1021/acs.joc.9b01961,10.1021/acs.orglett.9b03815,10.1038/s41557-019-0346-2,10.1021/acs.orglett.9b02190,10.1002/ejoc.201900471,10.1002/chem.201900822,10.1039/c9qo00335e,10.1002/adsc.201801685,10.1021/acs.joc.8b02738,10.1016/j.tet.2018.12.013,10.1002/anie.201811506,10.1039/c8ob02912a,10.1002/cjoc.201800500,10.6023/A18080333,10.1016/j.tet.2018.10.037,10.1021/acs.joc.8b01807,10.1039/c8nj02138d,10.1021/jacs.8b02745,10.1002/anie.201801085,10.1002/adsc.201701556,10.1021/acs.orglett.8b00173,10.1002/ajoc.201700446,10.1002/cjoc.201700633,10.1016/bs.aihch.2017.10.001,10.1021/acs.joc.7b01489,10.1002/asia.201701176,10.1002/adsc.201700798,10.1021/acscatal.7b02615,10.1002/anie.201706781,10.1021/jacs.7b06469,10.1002/aoc.3701,10.1002/chem.201702200,10.1039/c7cc01932g,10.1021/acs.orglett.7b01194,10.1016/j.tetlet.2017.04.005,10.1039/c7cc00891k,10.1016/j.tetlet.2016.12.013,10.1021/acs.organomet.6b00529,10.1016/j.tetlet.2016.09.049,10.1021/acscatal.6b01956,10.1007/s41061-016-0067-6,10.1002/anie.201604696,10.1021/acs.orglett.6b01904,10.1021/acs.orglett.6b01675,10.1039/c6gc01336h,10.1038/ncomms11676,10.6023/A15110736,10.1021/acs.orglett.6b00289,10.1016/bs.adomc.2016.08.001,10.1039/c6ob01721e,10.1039/c5nj01833a,10.1039/c6cc00176a,10.1070/RCR4611,10.1002/aoc.3394,10.1055/s-0035-1560586,10.1002/ejoc.201500734,10.1002/chem.201501543,10.6023/cjoc201503007,10.1021/acs.orglett.5b01612,10.1002/anie.201503140,10.1021/acs.joc.5b00669,10.1246/cl.141167,10.1002/ejic.201500148,10.1038/ncomms7526,10.1021/cs501502u,10.1002/ejoc.201403255,10.1039/c4cc06344a,10.1016/S1872-2067(14)60217-5,10.1039/c4gc01728e,10.1002/anie.201405058,10.1021/ol503111h,10.1063/1674-0068/27/06/640-646,10.1021/ja4127455,10.1021/ol501087m,10.1021/ol500696p,10.3184/174751914X13968892307636,10.1515/pac-2014-5032,10.1021/ja412107b,10.1039/c4ob00002a3/10/2022
406
427FALSEs0040-4039(97)10240-410.1016/s0040-4039(97)10240-4https://sci-hub.wf/10.1016/s0040-4039(97)10240-4https://doi.org/10.1016/s0040-4039(97)10240-4NiC-H ActivationLong9-MarTRUE593#N/A1997
12/8/1997Csp2-Csp2_arE-NuHXHIVinylArylIonic-CO3Nu-H_10.1002/anie.201308391,10.1002/anie.202011036,10.1021/acscatal.9b0223010.1016/j.reactfunctpolym.2021.104843,10.1007/s12039-020-01870-6,10.1002/anie.202011036,10.1007/s10562-020-03330-9,10.1021/acs.orglett.9b02130,10.1021/acscatal.9b02230,10.1021/acs.orglett.7b03713,10.1021/acs.orglett.7b03560,10.1002/ajoc.201700464,10.1002/anie.201706719,10.3184/174751917X15040898434417,10.3184/174751917X15040898434417,10.1002/anie.201606955,10.1039/c5cy02235e,10.1016/j.tet.2015.08.023,10.1002/ejoc.201500734,10.1107/S2053229615001680,10.1071/CH15459,10.1002/adsc.201400201,10.1002/anie.201308391,10.2174/138527212799859390,10.1039/c1dt10858a,10.1002/adsc.201000730,10.1021/cr100198w,10.1016/j.tet.2010.04.040,10.1039/b900697d,10.1002/adsc.200800662,10.1021/ja070321b,10.1002/anie.200603907,10.1021/om060043+,10.1016/j.molcata.2005.12.013,10.1016/j.tetlet.2005.08.072,10.1055/s-2005-869854,10.1016/j.synthmet.2005.04.003,10.1055/s-2005-864790,10.1021/om034067h,10.1016/j.tet.2003.12.012,10.1007/b96873,10.1023/A:1022124925590,10.1021/jo0201575,10.1021/ja003306e,10.1016/S0040-4039(00)01594-X,10.1021/cr9903048,10.1016/S1381-1169(00)00190-4,10.1039/a808136k,10.1016/S0040-4039(98)02225-4,10.1039/a803242d,10.1023/A:10190773001083/11/2022
407
17FALSEs41929-020-00560-310.1038/s41929-020-00560-3https://sci-hub.wf/10.1038/s41929-020-00560-3https://doi.org/10.1038/s41929-020-00560-3NiC-O ActivationLongTRUE91182021Martin, R
Highly selective synthesis of all-carbon tetrasubstituted alkenes by deoxygenative alkenylation of carboxylic acids
NATURE CATALYSIS
Tetrasubstituted olefins have been explored as chemical synthons and can sometime have useful photophysical properties, but are sometimes difficult to synthesize with high selectivity in mild conditions. Here the authors present a method to make tetrasubstituted olefins via dual photo- and nickel catalysis, without the need for an inert atmosphere. The synthesis of all-carbon tetrasubstituted olefins under mild reaction conditions is challenging because of the inevitable issues including significant steric hindrance and the uncontrolled Z/E stereoselectivity. In this paper, we report the synthesis of all-carbon tetrasubstituted alkenes from readily available carboxylic acids and alkenyl triflates with the synergistic catalysis of cyclo-octa-1,5-diene(tetramethyl-1,4-benzoquinone)nickel and visible light under an air atmosphere, thus avoiding the need for a glovebox or a Schlenk line. A wide range of aromatic carboxylic acids and cyclic and acyclic alkenyl triflates undergo the C-C coupling process smoothly, forming structurally diverse alkenes stereospecifically in moderate to good yields. The practicality of the method is further illustrated by the late-stage modification of complex molecules, the one pot synthesis and gram-scale applications. This is an important step towards the valuable utilization of carboxylic acids, and it also simplifies the experimental operation of metallophotoredox catalysis with moisture sensitive nickel(0) catalysis.
Barcelona Inst Sci & Technol
2/1/2021Csp2_ar-Csp2_arE-NuOZnOPivZnXArylArylNo baseNo BaseMedium0.33_x10.1021/jacs.1c0979710.1002/anie.202117843,10.1002/ejic.202101006,10.1021/jacs.1c09797,10.1002/asia.202100957,10.1039/d1ob00955a,10.1021/jacs.1c03763,10.1002/anie.202102481,10.1021/acs.orglett.1c003132/17/2022
408
308FALSEa908076g10.1039/a908076ghttps://sci-hub.wf/10.1039/a908076ghttps://doi.org/10.1039/a908076gNiC-O ActivationWilliam23-JunTRUE831582000Uemura, S
Overcoming limitations in dual photoredox/nickel-catalysed C-N cross-couplings due to catalyst deactivation
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Dual photoredox/nickel-catalysed C-N cross-couplings suffer from low yields for electron-rich aryl halides. The formation of catalytically inactive nickel-black is responsible for this limitation and causes severe reproducibility issues. Here, we demonstrate that catalyst deactivation can be avoided by using a carbon nitride photocatalyst. The broad absorption of the heterogeneous photocatalyst enables wavelength-dependent control of the rate of reductive elimination to prevent nickel-black formation during the coupling of cyclic, secondary amines and aryl halides. A second approach, which is applicable to a broader set of electron-rich aryl halides, is to run the reactions at high concentrations to increase the rate of oxidative addition. Less nucleophilic, primary amines can be coupled with electron-rich aryl halides by stabilizing low-valent nickel intermediates with a suitable additive. The developed protocols enable reproducible, selective C-N cross-couplings of electron-rich aryl bromides and can also be applied for electron-poor aryl chlorides.
10/25/1999Csp3-Csp2_arE-NuOBOAcB(OH)2AlkylArylKOHIonic-ORMedium0.317/6/2022
409
6FALSEb002547j10.1039/b002547jhttps://sci-hub.wf/10.1039/b002547jhttps://doi.org/10.1039/b002547jNiC-O ActivationLongTRUE533582000Uemura, S
Nickel(0)-catalyzed asymmetric cross-coupling reactions of allylic compounds with arylboronic acids
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Optically active oxazolinylferrocenylphosphines have been found to work quite effectively as chiral ligands in nickel(0)-catalyzed cross-coupling reactions of allylic compounds with arylboronic acids, which are known to behave as hard nucleophiles. The expected coupling products have been obtained in good yields with moderate enantioselectivities (up to 53% ee). This is the first example of asymmetric allylic substitution using organoboron compounds.
Kyoto Univ7/19/2000Csp3-Csp2_arE-NuOMgOAcMgXAlkylArylNo baseNo BaseMedium0.31_x10.1021/ja300031w,10.1002/chem.201502329,10.1021/ol702122d10.1002/ejic.202100820,10.6023/cjoc202106021,10.1021/acscatal.1c03449,10.1038/s41929-021-00589-y,10.1002/anie.202008071,10.1002/anie.202003755,10.1021/acs.orglett.0c01109,10.1021/acs.orglett.9b03633,10.6023/cjoc201809037,10.1002/cjoc.201800237,10.1055/S-0036-1591774,10.1016/j.tetlet.2016.04.027,10.1002/chem.201502329,10.1021/acs.chemrev.5b00162,10.1021/ja508067c,10.1039/c4dt01784f,10.1021/ja300031w,10.1007/3418_2011_15,10.1021/om200557c,10.1007/s11172-009-0150-z,10.1021/om800832r,10.1039/b907722g,10.1002/chem.200801879,10.1055/s-2008-1067222,10.1021/om800327j,10.1055/s-2008-1077903,10.1039/b809140d,10.1021/ol702122d,10.1021/ol0713842,10.5059/yukigoseikyokaishi.65.761,10.1021/ja0730718,10.1246/cl.2006.1368,10.1055/s-2005-864790,10.1016/j.tet.2004.09.010,10.1016/j.tetasy.2004.06.052,10.1039/B316819K,10.1016/S0957-4166(03)00520-2,10.1021/jo0345087,10.1021/ja035216q,10.1016/S0010-8545(02)00122-4,10.1021/jo026746s,10.1021/ja0295568,10.1021/om020814j,10.1002/1521-3765(20020816)8:16<3620::AID-CHEM3620>3.0.CO;2-P,10.1039/b203465d,10.1039/b107904b,10.1021/jo0158377Kelly3/11/2022
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Skrydstrup, T
Nickel(0)-catalysed asymmetric cross-coupling reactions of allylic compounds with Grignard reagents using optically active oxazolinylferrocenylphosphines as ligands
CHEMICAL COMMUNICATIONS
Optically active oxazolinylferrocenylphosphines work effectively as chiral P-N ligands in nickel(0)-catalysed cross-coupling reactions of allylic compounds with Grignard reagents, which are known to behave as hard nucleophiles, to give the expected coupling products in high yields and high enantioselectivities (30-100% chemical yield and 14-95% ee). These ligands are revealed to be more effective than optically active oxazolinylphenylphosphines which have only a central chirality.
Aarhus Univ8/22/2006Csp2-Csp2_arE-NuOB
OPO(OPh)2
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Direct synthesis of 1,1-diarylalkenes from alkenyl phosphates via nickel(0)-catalysed Suzuki-Miyaura coupling
CHEMICAL COMMUNICATIONS
A combination of Ni(COD)(2) and PCy3 promotes effectively the Suzuki - Miyaura cross coupling of 1-arylalkenyl phosphates with aryl boronic acids with yields attaining 99%.
Peking Univ1/25/2008TRUEFALSECsp2_ar-Csp3E-NuOMgOMeMgXArylAlkylNo baseNo BaseStrong-0.28_xxAdded by Long10.1021/jo1024464,10.1021/ol502583h,10.1021/ol4011757,10.1002/anie.201101191,10.1021/acs.orglett.5b02200,10.1002/chem.201003731,10.1021/ol503707m,10.1021/ja806244b,10.1021/ja8056503,10.1021/ol203322v,10.1016/j.tet.2012.04.005,10.1246/cl.150936,10.1002/anie.202012048,10.1021/acscatal.6b00801,10.1021/acs.orglett.6b02656,10.1021/ol901978e,10.1002/anie.201806790,10.1002/chem.201103050,10.1021/om300566m,10.1002/anie.200907287,10.1002/anie.201510497,10.1002/ejic.201900692,10.1021/ja200398c,10.1021/jacs.6b03253,10.1021/ja710944j,10.1002/anie.200803814,10.1021/ja903091g,10.1038/s41929-020-00560-3,10.1002/anie.201607646,10.1021/ol502682q,10.1002/chem.201103784,10.1002/anie.201402922,10.1039/c4cc08187k,10.1021/jacs.1c09797,10.1021/acs.organomet.5b00874,10.1039/c7cc06106d,10.1021/ja810157e,10.1021/ol9029534,10.1021/acscatal.8b03436,10.1021/ol302112q,10.1246/cl.2009.71010.1021/jacs.1c09797,10.1039/d1qo00549a,10.1021/acs.orglett.1c01280,10.1021/jacs.1c03038,10.1038/s41929-020-00560-3,10.1055/a-1349-3543,10.1055/s-0040-1705986,10.1002/anie.202012048,10.1021/acs.orglett.0c03507,10.1002/chem.202004132,10.1021/acscatal.0c03334,10.1021/acs.chemrev.0c00088,10.1021/acs.orglett.0c02236,10.1021/acs.joc.0c01274,10.1039/d0sc01641a,10.1039/d0sc01585g,10.1002/cjoc.201900506,10.1246/cl.200083,10.1016/j.heliyon.2020.e03446,10.1002/jccs.201900450,10.6023/A19050193,10.1002/adsc.201900745,10.1002/ejic.201900692,10.1039/c9dt00455f,10.1002/cjoc.201800575,10.1021/acs.organomet.8b00720,10.1007/3418_2018_19,10.1021/acscatal.8b03436,10.1021/acs.orglett.8b02351,10.1039/c8cc03665a,10.1002/anie.201806790,10.1021/acs.orglett.8b01696,10.1021/jacs.8b03669,10.1039/c8cc02325e,10.1021/acscatal.8b01224,10.1021/acs.orglett.8b00313,10.1021/acs.orglett.8b00674,10.1055/s-0037-1609093,10.1002/cjoc.201700664,10.1039/c7cc08709h,10.1021/acs.orglett.7b03753,10.1039/c7cy01205e,10.1070/RCR4795,10.1002/chem.201703266,10.1055/s-0036-1588568,10.1021/acs.orglett.7b03152,10.1021/acs.oprd.7b00241,10.1039/c7cc06106d,10.1021/acscatal.7b02025,10.1246/cl.170079,10.1039/c6cc09575e,10.1038/s41570-017-0025,10.1039/c6sc02895k,10.1021/acscatal.6b02964,10.1002/anie.201607646,10.1021/acs.orglett.6b02656,10.1002/chem.201604160,10.1002/asia.201600972,10.1002/chem.201602150,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1021/jacs.6b03253,10.1002/anie.201510497,10.1021/acscatal.5b02058,10.1016/bs.adomc.2016.07.001,10.1039/c5sc03359d,10.1021/acscatal.5b02089,10.1016/j.ccr.2015.02.004,10.1021/acs.organomet.5b00874,10.1246/cl.150936,10.1021/jacs.5b08621,10.1021/jacs.5b10119,10.1002/anie.201507373,10.1002/chem.201502114,10.1021/acs.orglett.5b02200,10.1002/ejoc.201500630,10.1002/adsc.201500304,10.1016/j.tet.2015.02.088,10.1021/acs.accounts.5b00051,10.1246/cl.141084,10.1021/ar500345f,10.1021/ol503707m,10.1039/c5qo00001g,10.1039/C5QO00243E,10.1039/c5nj01354b,10.1039/c5sc00305a,10.1039/c4cc08187k,10.1039/c4cc10084k,10.1002/anie.201402922,10.1021/ol502583h,10.1021/ol502682q,10.1021/ol5024344,10.1021/jo500619f,10.1016/j.tet.2014.03.061,10.1002/chem.201303809,10.1515/pac-2014-5038,10.1021/ja410883p,10.1039/c4cc00853g,10.1039/c4cs00206g,10.1002/ejoc.201301372,10.1021/ol4011757,10.1021/jo400424d,10.1021/ja312464b,10.1021/ja311940s,10.1021/ol303130j,10.1007/3418_2012_42,10.1039/c3sc22242j,10.1039/c3ob27128e,10.1039/c3cs35521g,10.1021/op300236f,10.1039/c3ra44884c,10.1002/adsc.201200364,10.1021/om300566m,10.1021/ol302112q,10.1002/chem.201201125,10.1016/j.tet.2012.04.005,10.1021/om300369f,10.1021/ol3009842,10.1021/ol300671y,10.1016/j.jphotochem.2012.02.008,10.1021/ja300326t,10.1021/ol203322v,10.1002/chem.201103784,10.1021/ol2033306,10.1039/c2cc34454h,10.1002/chem.201103050,10.1002/anie.201203778,10.1021/ja207759e,10.1016/j.tet.2011.06.001,10.1246/cl.2011.1001,10.1021/jo201339z,10.1002/cctc.201100181,10.1002/cctc.201100087,10.1021/ol2012007,10.1021/ja200398c,10.1126/science.1200437,10.1002/chem.201003731,10.1021/jo1024464,10.1021/cr100259t,10.1002/anie.201101191,10.1002/anie.201103599,10.1039/c0cc05169a,10.1002/chem.201001943,10.1002/chem.201002273,10.1021/ar100082d,10.1021/jo101718v,10.1021/ol1018739,10.1021/jo100877j,10.1021/jo1007898,10.1055/s-0030-1258116,10.1021/ol9029534,10.1002/anie.200901317,10.1002/anie.200907287,10.1021/ol901978e,10.1021/ja903091g,10.1246/cl.2009.710,10.1021/ja810157e,10.1002/ejoc.200801004,10.1021/ja806244b,10.1021/ja8056503,10.1021/ja804804p,10.1055/s-2008-1067182,10.1016/j.tetlet.2008.04.117,10.1021/ja710944j,10.1002/anie.200801447,10.1002/anie.200803814Kelly11/9/2021
418
120FALSEb803072c10.1039/b803072chttps://sci-hub.wf/10.1039/b803072chttps://doi.org/10.1039/b803072cNiC-O ActivationGerryTRUE581972008Knochel, P
Methylation of arenes via Ni-catalyzed aryl C-O/F activation
CHEMICAL COMMUNICATIONS
Aryl C-O and C-F can be transformed into C-Me via Ni-catalyzed coupling with MeMgBr under mild conditions.
Univ Munich4/24/2008Csp2_ar-Csp3-ring(s)E-NuOZnOTsZnXArylBenzylNo baseNo BaseWeak0.36_10.1055/s-0041-1737275,10.1002/slct.202101388,10.1016/j.tetlet.2020.152123,10.3390/molecules24040696,10.1021/jacs.8b05143,10.1021/acscatal.8b01224,10.1021/acs.joc.7b02033,10.1016/j.tetlet.2017.05.083,10.1021/acscatal.6b02964,10.1002/chem.201602668,10.1002/adsc.201600378,10.1021/acs.orglett.6b01134,10.1002/anie.201511975,10.1055/s-0035-1561198,10.1016/j.tet.2016.02.005,10.1021/jacs.6b00250,10.2174/1389557516666160823143243,10.1039/c5cc10272c,10.1021/acs.joc.5b01978,10.1055/s-0034-1378867,10.1021/jacs.5b05076,10.1021/ol503607h,10.1039/c4sc03106g,10.1055/s-0034-1378672,10.1021/om500637k,10.1055/s-0034-1379025,10.1016/j.ica.2014.05.023,10.1021/cr400367p,10.1039/c4ra04059g,10.1039/c4cc05376a,10.1039/c4gc00005f,10.1039/c4ra01341g,10.1021/cr3002966,10.1039/c3ra42955e,10.1039/c3ra40413g,10.1021/jo302207b,10.1007/s11172-012-0162-y,10.1002/chem.201101037,10.3762/bjoc.7.147,10.1021/ja205547h,10.1007/s11172-011-0239-z,10.1002/asia.201100153,10.1021/om200004a,10.1039/c1cc11087j,10.1080/00397911.2010.488310,10.1002/ijch.201000032,10.1007/s10562-010-0385-1,10.1021/jo1003373,10.1002/anie.201002116,10.1039/b922280d,10.1039/c0cc00778a,10.1016/j.poly.2009.05.080,10.1002/chem.200900575,10.1021/jo8018686,10.1039/b809626k,10.1039/b812396a,10.1002/asia.200800161Kelly2/15/2022
419
210FALSEc0cc01716g10.1039/c0cc01716ghttps://sci-hub.wf/10.1039/c0cc01716ghttps://doi.org/10.1039/c0cc01716gNiC-O ActivationKellyTRUE1338382010Weix, DJ
Nickel-catalyzed cross-coupling reactions of benzylic zinc reagents with aromatic bromides, chlorides and tosylates
CHEMICAL COMMUNICATIONS
Benzylic zinc reagents prepared by direct insertion of zinc to benzylic chlorides in the presence of LiCl undergo smooth crosscoupling reactions with aromatic chlorides, bromides and tosylates using Ni(acac)(2) and PPh(3) as a catalyst system.
Univ Rochester6/28/2010Csp2-Csp2E-EOOOAcOAcVinylVinylNo baseNo BaseMedium0.31_10.1039/d1cc02837e,10.1039/c9sc03347e,10.1002/chem.201102984,10.1021/acscatal.9b03352,10.1021/acs.joc.5b00135,10.1021/jacs.0c01330,10.1021/ja5029793,10.1039/c7cc06717h10.1002/anie.202200215,10.1021/acs.orglett.2c00207,10.1002/anie.202201370,10.1039/d2ra00010e,10.1002/anie.202113209,10.1002/ejic.202100820,10.1002/anie.202112454,10.1002/hlca.202100177,10.1002/anie.202112876,10.1021/acs.orglett.1c02874,10.1021/acscatal.1c03265,10.1039/d1cc02837e,10.1021/jacs.1c06271,10.1021/acs.joc.1c00910,10.1002/hlca.202100056,10.1021/acs.organomet.1c00280,10.1002/anie.202104051,10.1002/anie.202102481,10.1021/acscatal.1c01416,10.1002/aocs.12484,10.1055/a-1467-2432,10.1021/acs.orglett.1c00058,10.1055/a-1374-9384,10.1007/s10562-020-03496-2,10.1055/s-0040-1707342,10.1002/anie.202010737,10.1021/acsomega.0c04181,10.6023/cjoc202005072,10.1021/acs.orglett.0c02165,10.1021/acscatal.0c01842,10.1021/jacs.0c04812,10.1002/cctc.201902290,10.1021/jacs.0c02673,10.1002/cjoc.202000084,10.1021/jacs.0c01330,10.1039/c9sc03347e,10.1021/acscatal.9b03352,10.1002/ajoc.201900435,10.1021/acs.oprd.9b00232,10.1021/acscatal.9b01785,10.1002/ajoc.201900254,10.1021/acs.joc.9b00649,10.1016/j.ccr.2019.01.005,10.3390/molecules24081458,10.1055/s-0037-1610356,10.6023/cjoc201806038,10.1021/jacs.8b13499,10.6023/cjoc201808014,10.1021/jacs.8b12025,10.1021/acs.orglett.8b02980,10.1021/jacs.8b08190,10.1021/acs.joc.8b00631,10.1039/c8sc00210j,10.1021/acs.orglett.8b00235,10.1055/s-0036-1591853,10.1039/c7cc06717h,10.1002/cjoc.201700071,10.1002/ejoc.201601571,10.1002/adsc.201601271,10.1055/s-0036-1588132,10.1002/asia.201601712,10.1021/acs.joc.6b02830,10.1002/chem.201603832,10.1039/c6qo00529b,10.1039/c6nj03265f,10.1055/s-0035-1562442,10.1016/j.tetlet.2016.06.092,10.1007/s41061-016-0042-2,10.1002/adsc.201600213,10.1021/jacs.6604088,10.1002/chem.201503926,10.1039/c6gc01113f,10.1039/c6dt00252h,10.1055/s-0035-1560324,10.1021/acs.orglett.5b02716,10.1055/s-0035-1560712,10.1515/hc-2015-0058,10.1021/acs.accounts.5b00057,10.1016/j.tetlet.2015.03.106,10.1021/acs.orglett.5b00766,10.1016/j.polymer.2015.02.037,10.1021/acs.joc.5b00135,10.1039/c4sc03106g,10.1039/c5qo00224a,10.1002/tcr.201402058,10.1002/chem.201405223,10.1021/jo501925s,10.1021/ja508067c,10.1021/ol502207z,10.1055/s-0033-1339126,10.1021/jo500507s,10.1021/ja5029793,10.1016/j.jorganchem.2013.12.047,10.1039/c3ob41918e,10.1021/ol403083e,10.1021/jo401936v,10.1055/s-0033-1339435,10.1016/j.tet.2013.04.073,10.1021/ja4030462,10.1021/ja311045f,10.1021/ja309176h,10.1016/j.tet.2012.10.044,10.1039/c3sc51098k,10.1002/chem.201200190,10.1021/ja301769r,10.1021/ic2027219,10.1021/ol300217x,10.1002/ejic.201101036,10.1002/chem.201102984,10.1021/ic201184x,10.1021/ja205167e,10.1021/ol200881v,10.1021/ja200270k,10.1021/ol200617f,10.1002/ejoc.201100175,10.1021/jo200023r,10.1002/anie.201007963,10.1002/anie.201104390,10.1039/c1sc00368b,10.1021/ja1083392 Long 2/14/2022
420
60FALSEc0cc02173c10.1039/c0cc02173chttps://sci-hub.wf/10.1039/c0cc02173chttps://doi.org/10.1039/c0cc02173cNiC-O ActivationLongTRUE371272011Nakao, Y
Nickel-catalyzed, sodium iodide-promoted reductive dimerization of alkyl halides, alkyl pseudohalides, and allylic acetates
CHEMICAL COMMUNICATIONS
The first general method for the reductive dimerization of alkyl halides, alkyl mesylates, alkyl trifluoroacetates, and allylic acetates is reported which proceeds with low catalyst loading (0.5 to 5 mol%), generally high yields (80% ave yield), and good functional-group tolerance.
Kyoto Univ8/23/2010Csp2_ar-Csp2_arE-NuOSiOTs
(trialkyl)silanes
ArylArylIonic-CO3Weak0.36_10.1039/c6sc03902b10.1021/acsanm.1c03736,10.1055/a-1379-1584,10.1002/ejoc.202001458,10.1021/acs.chemrev.0c00245,10.1021/acs.joc.0c01277,10.5059/yukigoseikyokaishi.76.1185,10.1039/c8cy00996a,10.1016/j.jfluchem.2018.07.008,10.24820/ark.5550190.p010.746,10.1055/s-0036-1589008,10.1007/s13738-017-1050-z,10.1021/acscatal.6b02374,10.1246/cl.160439,10.1002/adsc.201600590,10.2174/1570178613666160812102130,10.1246/cl.150359,10.1016/j.tetlet.2015.01.131,10.1039/c3dt53391c,10.1021/ol5007086,10.1515/pac-2014-5031,10.1246/cl.130919,10.1080/00397911.2013.862835,10.1021/ol402047d,10.1021/ol400922j,10.1002/ajoc.201300031,10.1246/cl.2013.45,10.1021/ol303222s,10.1039/c3cy20826e,10.1016/j.tetlet.2012.09.072,10.1021/ja3096174,10.1246/cl.2012.1503,10.1016/j.tetlet.2012.01.051,10.1016/j.tetlet.2011.10.126,10.1039/c1cs15122c2/10/2022
421
203FALSEc0cc03107k10.1039/c0cc03107khttps://sci-hub.wf/10.1039/c0cc03107khttps://doi.org/10.1039/c0cc03107kNiC-O ActivationGerryTRUE1128332010Tu, T
Nickel-catalysed cross-coupling reaction of aryl(trialkyl)silanes with aryl chlorides and tosylates
CHEMICAL COMMUNICATIONS
Using highly stable, readily accessible, and recyclable 2-(2-hydroxyprop-2-yl) cyclohexyl-substituted arylsilanes activated by a mild carbonate base, nickel-catalysed silicon-based aryl-aryl cross-coupling reaction proceeds for the first time with inexpensive aryl chlorides and tosylates in a highly chemoselective manner.
Fudan Univ9/8/2010Csp2_ar-Csp2_arE-NuOBOTsB(OH)2ArylArylK3PO4Ionic-PO4Weak0.36TM10.1021/om300566m,10.1002/ejoc.201200444,10.1039/c3cc46663a,10.1021/acs.orglett.6b01398,10.1021/jo2022982,10.1002/adsc.201100151,10.1021/jo1024464,10.1021/jo501291y10.1039/d1ob01619a,10.1007/s10562-021-03787-2,10.1039/d1nj01698a,10.1016/j.jorganchem.2021.121754,10.1134/S1023193521020075,10.1002/slct.202003634,10.1002/chem.202004132,10.1016/j.ica.2020.119457,10.1016/j.ica.2020.119446,10.1007/s11172-020-2818-3,10.1002/slct.201904819,10.1021/acs.orglett.9b02858,10.1016/j.poly.2018.10.028,10.1002/ejic.201801179,10.1016/j.apenergy.2018.09.006,10.1002/asia.201800759,10.1002/cctc.201702019,10.1002/celc.201800407,10.1016/j.jorganchem.2018.03.030,10.1002/aoc.4054,10.1016/j.catcom.2017.09.021,10.1002/asia.201701303,10.1016/j.jorganchem.2017.07.026,10.1016/j.jorganchem.2017.03.045,10.1039/c7dt01912b,10.1007/s11172-017-1920-7,10.1002/aoc.3671,10.1021/acsomega.7b00725,10.1021/acscatal.7b00860,10.1016/j.ccr.2017.03.007,10.1039/c6nj03789e,10.1016/j.cclet.2016.09.006,10.1002/asia.201601537,10.1039/c6dt03944h,10.1016/j.jorganchem.2016.11.005,10.1021/acs.orglett.6b01398,10.1016/j.jorganchem.2016.02.019,10.1021/acs.joc.5b02667,10.1007/3418_2015_127,10.1039/c5dt04429d,10.6023/cjoc201506029,10.1021/acscatal.5b01782,10.1002/aoc.3350,10.1016/j.jorganchem.2015.04.019,10.1002/cctc.201403057,10.1002/aoc.3297,10.1016/j.ica.2014.11.005,10.3390/molecules20057528,10.1002/marc.201400699,10.1016/j.molcata.2014.10.031,10.1021/cs5014927,10.1016/bs.adomc.2015.02.002,10.1039/c5gc01170a,10.1039/c4cy01736f,10.1039/C5CC00196J,10.1039/c5dt01358e,10.1016/j.jorganchem.2014.05.022,10.1002/ejoc.201402919,10.1021/jo501291y,10.1002/chem.201403103,10.1055/s-0033-1338635,10.1016/j.tet.2014.02.051,10.1016/j.molcata.2014.01.001,10.1039/c4qo00233d,10.1039/c4qo00253a,10.1039/c4cc05151c,10.1039/c4cc04743e,10.1039/c3cc49402k,10.6023/cjoc201307035,10.1039/c3ra45790g,10.1039/c3ob41376d,10.1021/jp409794a,10.1021/jo400803s,10.1021/ol401550h,10.1021/ol4010195,10.1016/j.tet.2012.11.003,10.1039/c3cc46663a,10.1016/B978-0-12-407777-5.00002-6,10.1002/cctc.201200417,10.1039/c3cs35521g,10.1021/om300566m,10.1021/ol3019665,10.1016/j.tet.2012.05.075,10.1021/jo301270t,10.1002/ejoc.201200444,10.1016/j.ultsonch.2011.08.013,10.1021/om201271y,10.1002/ejic.201101036,10.1021/jo2022982,10.1071/CH12044,10.1039/c2dt12243j,10.1002/ejoc.201101527,10.1039/c2cc15972d,10.1016/j.jorganchem.2011.09.008,10.1002/adsc.201100151,10.1002/adsc.201100101,10.1002/adsc.201100134,10.1016/j.poly.2011.01.007,10.1055/s-0030-1259723,10.1021/jo1024464,10.1002/anie.201100620,10.1039/c1cc15503b,10.1002/chem.201002273,10.1039/c1dt10928f,10.1039/c0dt01083aKelly1/11/2022
422
445FALSEncomms940410.1038/ncomms9404https://sci-hub.wf/10.1038/ncomms9404https://doi.org/10.1038/ncomms9404NiC-H ActivationGerry15-MarTRUE611#N/A2015
9/1/2015Csp3-Csp3-ring(s)HHHHAlkylBenzylNo baseNo BaseNu-H_10.1039/d1gc01210j,10.1002/adsc.202001441,10.1055/a-1331-7285,10.1021/acs.joc.0c01940,10.1016/j.tet.2020.131621,10.1039/d0sc03791e,10.1002/adsc.202000975,10.1002/adsc.202000974,10.1002/anie.202010157,10.1021/acs.joc.0c01816,10.1055/s-0040-1707245,10.1021/acs.orglett.0c01853,10.1021/acs.orglett.0c01715,10.1016/j.isci.2020.101153,10.1021/acs.organomet.0c00021,10.1021/jacs.0c02707,10.1039/d0cc01017k,10.1021/acs.joc.0c00132,10.1021/acs.chemrev.9b00495,10.1021/acs.joc.9b02797,10.1039/c9ra08752d,10.1016/j.tetlet.2019.151225,10.1021/acs.joc.9b02299,10.1039/c9sc03425k,10.1039/c9ra05678e,10.6023/cjoc201903006,10.1002/tcr.201800093,10.1055/s-0037-1612417,10.1016/j.tetlet.2019.04.041,10.1021/acscatal.8b04933,10.1002/anie.201811023,10.1002/ejoc.201800896,10.1021/acs.orglett.8b03044,10.1021/acscatal.8b02361,10.1055/s-0037-1610073,10.1016/j.cclet.2018.05.011,10.1055/s-0036-1591586,10.1002/anie.201711291,10.1002/chem.201800543,10.1021/acs.orglett.8b00874,10.1039/c7cc08512e,10.1039/c7ob02921g,10.1002/anie.201708893,10.1021/acs.orglett.7b02968,10.6023/cjoc201704049,10.1021/acs.orglett.7b02170,10.1002/adsc.201700654,10.1039/c7cc04252c,10.1021/acs.chemrev.6b00620,10.1021/acscatal.7b01072,10.1039/c7cc01309d,10.1021/acs.organomet.7b00143,10.1016/j.tetlet.2017.01.079,10.1039/c7ra05303g,10.1002/adsc.201600926,10.1007/s41061-016-0053-z,10.1002/asia.201600193,10.1038/ncomms11676,10.1021/acs.joc.5b02838,10.1016/j.cclet.2015.12.0213/15/2022
423
446FALSEadsc.20110048710.1002/adsc.201100487https://sci-hub.wf/10.1002/adsc.201100487https://doi.org/10.1002/adsc.201100487NiC-H ActivationShihong15-MarTRUE5510#N/A2011
12/1/2011Csp2_ar-Csp3HXHClHetAlkylt-BuOLiIonic-OtBuNu-H_10.1021/acscatal.8b04267,10.1021/acs.organomet.6b00201,10.1021/acscatal.6b01120,10.1002/anie.201510743,10.1021/acscatal.6b02003,10.1039/c5sc03704b,10.1021/ja401344e,10.1002/anie.201309584,10.1039/c5sc01589h,10.1002/anie.20170908710.1002/tcr.202100113,10.1021/acscatal.0c05580,10.1002/anie.202009527,10.1039/d0qo00567c,10.1021/acs.orglett.0c02609,10.1002/anie.202004958,10.1021/acs.organomet.0c00161,10.1016/j.chempr.2020.04.005,10.1055/s-0037-1611895,10.1002/anie.201904214,10.1021/acs.organomet.9b00060,10.1002/anie.201806631,10.1021/acs.chemrev.8b00507,10.3390/catal9020173,10.1021/acs.orglett.8b03924,10.1021/acscatal.8b04267,10.1002/chem.201805441,10.1021/acscatal.8b03770,10.1002/asia.201800504,10.1021/acs.organomet.8b00025,10.1002/anie.201709087,10.1039/c7cc05011a,10.1007/s12039-017-1338-7,10.1055/s-0036-1588493,10.1039/c6sc05622a,10.1021/acs.joc.6b02211,10.1002/chem.201603092,10.1021/acscatal.6b02003,10.1021/acscatal.6b01120,10.1002/chem.201601482,10.1021/acs.organomet.6b00201,10.1021/acs.joc.6b00715,10.1002/anie.201510743,10.1021/jacs.6b00250,10.1039/c5sc03704b,10.1002/anie.201504735,10.1055/s-0034-1379927,10.1016/j.tet.2015.03.066,10.1002/chem.201500552,10.1021/jo5025317,10.1039/c5sc01589h,10.1002/anie.201408355,10.1002/anie.201309584,10.1002/chem.201301409,10.1021/ja401466y,10.1021/ja401344e,10.1002/chem.201203413,10.1002/anie.201209312,10.1039/c3cc43915a,10.1021/ol302640e,10.3762/bjoc.8.202,10.1055/s-0031-1290382,10.1021/ol300348w,10.1039/c2cc35758e,10.1002/anie.2012008093/17/2022
424
448FALSEacscatal.9b0223010.1021/acscatal.9b02230https://sci-hub.wf/10.1021/acscatal.9b02230https://doi.org/10.1021/acscatal.9b02230NiC-H ActivationShihong15-MarTRUE382#N/A2019
8/1/2019Csp2-Csp2_arHXHBrVinylArylpyridineNitrogenNitrogen(neutral)Nu-H_10.1002/anie.202011036,10.1039/d1cc00634g10.1021/acscatal.1c05441,10.1021/acs.orglett.1c03500,10.1016/j.xcrp.2021.100476,10.1039/d1cs00223f,10.1002/anie.202016310,10.1039/d1cc00634g,10.1039/d0nj06027e,10.1002/anie.202014244,10.1002/anie.202011036,10.1002/adsc.202000820,10.1039/d0cc04650g,10.1002/chem.202001318,10.1002/anie.202004958,10.6023/cjoc201911029,10.1021/jacs.0c01475,10.1021/acs.accounts.9b005133/17/2022
425
449FALSEanie.20181075710.1002/anie.201810757https://sci-hub.wf/10.1002/anie.201810757https://doi.org/10.1002/anie.201810757NiC-H ActivationShihong15-MarTRUE211#N/A2018
12/17/2018Csp2-Csp3HXHBrVinylAlkylEt3NNitrogenNitrogen(neutral)Nu-H_10.1021/acscatal.9b0223010.1021/acscatal.1c04705,10.1021/acscatal.1c04705,10.1021/acs.joc.1c01258,10.1002/adsc.202001325,10.1055/s-0040-1706602,10.1055/s-0040-1705966,10.1021/acs.orglett.0c03030,10.1002/adsc.202000820,10.1007/s10562-020-03413-7,10.1021/acs.orglett.0c02909,10.1021/acs.joc.0c00077,10.1021/acs.orglett.0c00945,10.1002/cjoc.201900509,10.1002/adsc.201901398,10.1016/j.tetlet.2019.151283,10.1007/s10593-019-02541-2,10.1002/ejoc.201900940,10.1016/j.tet.2019.05.047,10.1021/acscatal.9b02230,10.1021/acs.orglett.9b00600,10.1021/acs.accounts.9b00044,10.1055/s-0037-16116593/17/2022
426
52FALSEc1cc11193k10.1039/c1cc11193khttps://sci-hub.wf/10.1039/c1cc11193khttps://doi.org/10.1039/c1cc11193kNiC-O ActivationShihongTRUE343282011Shi, ZJ
A pyridine-bridged bis-benzimidazolylidene pincer nickel(II) complex: synthesis and practical catalytic application towards Suzuki-Miyaura coupling with less-activated electrophiles
CHEMICAL COMMUNICATIONS
A novel robust pyridine-bridged bis-benzimidazolylidene nickel pincer complex 3 accessible from inexpensive, commercially available precursors efficiently catalyzes the first practical Suzuki-Miyaura cross-coupling reactions with various less-reactive electrophiles ArX ( X = Br, Cl, OTs and OMs) and even tolerates electron-rich, sterically demanding and heterocyclic arenes in the presence of catalytic amounts of PPh3.
Peking Univ5/27/2011Csp2-Csp2_arE-NuOBOPivB(OH)2
Carbonyl
ArylNaOtBuIonic-OtBuMedium0.33_x10.1021/ja307045r,10.1039/c6ob01299j,10.1021/acs.orglett.6b0139810.1021/acs.joc.1c02446,10.1021/acs.joc.1c02446,10.6023/cjoc202106021,10.1039/d1qo01106e,10.6023/cjoc202010023,10.1016/j.tet.2021.132034,10.1039/d0qi01411g,10.1039/d0qo00543f,10.1039/c9ob02258a,10.1002/chem.201900582,10.1021/acs.orglett.7b03753,10.1038/s41570-017-0025,10.1007/s12274-016-1176-9,10.1021/acs.orglett.6b01398,10.1039/c6ob01299j,10.1002/anie.201505136,10.1021/acs.joc.5b00825,10.1016/j.tet.2015.05.068,10.1021/ar500345f,10.1039/c5qo00241a,10.1002/anie.201310272,10.1515/pac-2014-5038,10.1021/ja412107b,10.1021/cs4009946,10.1021/ja410883p,10.1039/c4ra00120f,10.1002/ejoc.201300610,10.1021/ol401416r,10.1021/ja312087x,10.1039/c3sc22242j,10.1039/c3cs35521g,10.1002/ejoc.201200951,10.1021/ja307045r,10.1021/ol20327841/6/2022
427
455FALSEc8sc04437f10.1039/c8sc04437fhttps://sci-hub.wf/10.1039/c8sc04437fhttps://doi.org/10.1039/c8sc04437fNiDeletedShihong16-MarFALSE411552019Mashima, K#N/A1/28/201910.1021/jacs.9b1120810.1055/s-0041-1737761,10.1021/jacs.1c10932,10.1021/acs.inorgchem.1c02925,10.1039/d1dt03331j,10.1021/acs.joc.1c01866,10.1039/d1gc03060d,10.1038/s41598-021-90478-y,10.1039/d1ob00610j,10.1039/d1qo00162k,10.1002/asia.202100003,10.1016/j.tetlet.2020.152749,10.1021/acs.chemrev.0c00301,10.1039/d0ob01928c,10.7536/PC200607,10.1021/acscatal.0c03903,10.1039/d0nj01996h,10.1055/s-0040-1705943,10.1016/j.tet.2020.131388,10.1038/s41467-020-17939-2,10.1021/acsomega.0c01002,10.1016/j.jorganchem.2020.121337,10.1016/j.ijbiomac.2020.04.003,10.1021/jacs.0c03184,10.1002/adsc.202000369,10.1039/d0qo00282h,10.1021/acs.joc.0c00269,10.1021/acs.organomet.0c00034,10.1055/s-0039-1691590,10.1039/d0sc00964d,10.1039/c9cc10057a,10.1021/acscatal.9b04586,10.1021/jacs.9b11208,10.1016/j.trechm.2019.08.004,10.1002/ajoc.201900223,10.1055/s-0037-1611793,10.1021/acs.accounts.8b00638#N/A
428
122FALSEc1sc00026h10.1039/c1sc00026hhttps://sci-hub.wf/10.1039/c1sc00026hhttps://doi.org/10.1039/c1sc00026hNiC-O ActivationKelly17-FebTRUE628452011Doyle, AG
Arylation of alpha-pivaloxyl ketones with arylboronic reagents via Ni-catalyzed sp(3) C-O activation
CHEMICAL SCIENCE
A Suzuki-Miyaura coupling of alpha-pivaloxyl ketones via Ni-catalyzed sp(3) C-O activation to produce alpha-aryl ketones is developed. This study offers a convenient method to construct alpha-arylation products from readily available alpha-hydroxyl carbonyl compounds.
Princeton Univ2/21/2011xCsp3-Csp2_arE-NuOBOEtB(OH)2AllylArylNo baseNo BaseStrong-0.24_x10.1002/asia.201100971,10.1038/NCHEM.2741,10.1021/ol300364s,10.1021/ja3013825,10.1021/jacs.6b11412,10.1021/ol4031364,10.1021/ol201248c,10.1039/c6sc00702c10.1002/ejic.202100820,10.6023/cjoc202106021,10.1021/acs.organomet.1c00505,10.1055/a-1577-7638,10.1039/c9cs00571d,10.6023/cjoc202004015,10.1021/acs.orglett.9b04220,10.1021/acs.orglett.9b03503,10.1021/acs.chemrev.9b00214,10.1021/acs.orglett.9b02034,10.1055/s-0037-1610682,10.6023/cjoc201809037,10.1021/acscatal.8b00933,10.6023/cjoc201803001,10.1021/jacs.7b12212,10.1039/c7cc04397j,10.1039/c7ob01793f,10.1038/NCHEM.2741,10.1021/jacs.6b11412,10.1070/RCR4727,10.1070/RCR4628,10.1016/j.tet.2016.08.041,10.1021/acscatal.6b01725,10.1002/adsc.201501015,10.1039/c6ob01355d,10.1039/c6sc01457g,10.1039/c6sc00702c,10.1002/anie.201505699,10.1021/acs.chemrev.5b00162,10.1021/acs.inorgchem.5b00893,10.1039/c5cc05209b,10.1016/j.jorganchem.2014.09.032,10.1002/ejoc.201403043,10.1002/adsc.201400234,10.1126/science.1255525,10.1002/aoc.3144,10.1021/ol500701n,10.1002/anie.201310193,10.1021/cs401164z,10.1021/cs400641k,10.1021/ol4031364,10.1039/c4ra02941k,10.1039/c3dt53012d,10.1021/ol402685g,10.1002/ejoc.201301264,10.1002/anie.201303994,10.1021/ic302153s,10.1021/ja3079362,10.1021/om300671j,10.1021/ja3013825,10.1002/asia.201100971,10.1021/jo3003503,10.1021/jo300162c,10.1021/ol300364s,10.1021/jo202339v,10.1039/c2cc17744g,10.1021/ol2028702,10.1021/ja205174c,10.1021/ol201248cKelly1/11/2022
429
212FALSEc1sc00230a10.1039/c1sc00230ahttps://sci-hub.wf/10.1039/c1sc00230ahttps://doi.org/10.1039/c1sc00230aNiC-O ActivationKellyTRUE12927542011Garg, NK
Transition metal-catalyzed cross coupling with N-acyliminium ions derived from quinolines and isoquinolines
CHEMICAL SCIENCE
A Ni(0) catalyst facilitates efficient C-C bond formation between a wide range of p-neutral and p-deficient aryl boronic acids and N-acyliminium precursors derived from quinoline and isoquinoline. The reaction proceeds under mild conditions and is tolerant of common organic functional groups. In addition, a simple one-pot protocol amenable to the direct use of substituted quinolines is described. Consistent with preliminary data revealing a mild, organoboronate-mediated racemization of enantioenriched N-acyliminium precursors, initial results indicate that a chiral phosphoramidite-ligated nickel catalyst promotes enantioselective arylation of racemic substrate with no evidence of a kinetic resolution during catalysis.
Univ Calif Los Angeles
6/9/2011TRUEFALSEFALSEyyCsp2_ar-Nsp3E-NuOH
OCONEt2
HAryl
Morpholine
NaOtBuIonic-OtBuMedium0.31_10.1002/chem.201605095,10.1002/adsc.201400460,10.1021/acscatal.7b00941,10.1021/acscatal.8b03436,10.1021/acscatal.6b00865,10.1002/anie.201806790,10.1021/acs.orglett.7b00556,10.1002/anie.201410875,10.1021/jacs.7b04279,10.1038/ncomms11073,10.1038/s41467-020-20725-9,10.1021/ja210249h,10.1021/jacs.1c09797,10.1038/nature14615,10.1021/ol403209k,10.1016/j.tet.2012.04.005,10.1021/ol401727y,10.1021/cs501045v,10.1021/acscatal.8b01879,10.1002/chem.201103050,10.1021/jacs.9b02751,10.1021/ol301847m,10.1021/acs.joc.6b01627,10.1021/acscatal.7b02817,10.1021/jacs.7b04973,10.1021/acs.orglett.6b02656,10.1021/acscatal.6b0080110.1002/slct.202103723,10.1021/jacs.1c09797,10.1039/d0nj05711h,10.1038/s41467-020-20725-9,10.1021/acscatal.0c03888,10.1021/acscatal.0c03334,10.1021/acs.chemrev.0c00088,10.1021/acs.orglett.0c02320,10.1039/d0nj01610a,10.1016/j.mcat.2020.110915,10.1039/d0sc01585g,10.1002/chem.201904288,10.1039/c9cy01285k,10.1021/acs.orglett.9b02621,10.1002/ejoc.201900057,10.1021/acscatal.9b02760,10.1055/s-0037-1611732,10.1021/jacs.9b02751,10.1021/acs.chemrev.8b00361,10.1021/acs.organomet.8b00720,10.1007/3418_2018_19,10.1021/acs.orglett.8b03698,10.1021/acscatal.8b03436,10.1002/anie.201806790,10.1021/acscatal.8b01879,10.1016/j.jorganchem.2018.01.019,10.1021/acscatal.8b00856,10.1002/aoc.4273,10.1021/acs.orglett.8b00060,10.1021/acs.chemrev.7b00588,10.1021/acscatal.7b03215,10.1002/aoc.3855,10.1021/acscatal.7b02817,10.1002/anie.201706982,10.1021/acs.organomet.7b00642,10.1021/jacs.7b04973,10.1039/c7ob01791j,10.1002/adsc.201700672,10.1021/acscatal.7b02025,10.1021/jacs.7b04279,10.1055/s-0036-1590819,10.1021/acs.orglett.7b01549,10.1021/acscatal.7b00941,10.1039/c7qo00068e,10.1002/ejoc.201700660,10.1016/j.mcat.2016.12.023,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1021/acscatal.6b03543,10.1016/j.jorganchem.2016.12.029,10.1021/acs.orglett.6b03703,10.1021/acscatal.6b03277,10.1021/acs.jpcb.6b08644,10.1021/acscatal.6b02964,10.1002/chem.201605095,10.1021/acs.orglett.6b02656,10.1002/ejoc.201600933,10.1021/acs.joc.6b01627,10.1021/acs.organomet.6b00650,10.1002/chem.201601584,10.1002/tcr.201500305,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1021/acscatal.6b00865,10.1021/acs.joc.6b00289,10.1021/acs.joc.6b00329,10.1038/ncomms11073,10.1021/acscatal.5b02021,10.1039/c6ob00073h,10.1039/c5sc03359d,10.1039/c6ra14367a,10.1021/acs.oprd.5b00314,10.1002/adsc.201500515,10.1002/ejoc.201500734,10.1038/nature14615,10.1021/acs.orglett.5b01229,10.1016/j.tet.2015.02.088,10.1002/ejoc.201500226,10.1002/anie.201500404,10.1002/anie.201410875,10.1246/cl.141084,10.1021/ed500158p,10.1021/ja512498u,10.1016/j.molcata.2014.10.031,10.1039/c4cc06445c,10.1021/ja5099935,10.1002/adsc.201400460,10.1021/ol5024344,10.1021/cs501045v,10.1002/anie.201404355,10.1002/adsc.201400201,10.1021/ja4127455,10.1021/jo402723e,10.1021/ja4118413,10.1021/ja411911s,10.1021/ja410883p,10.1021/ol403209k,10.1039/c4qo00233d,10.1039/c4ob00475b,10.1039/c3dt52412d,10.1002/adsc.201300485,10.1595/147106713X672311,10.1016/j.tetlet.2013.06.061,10.1021/ol401727y,10.1021/ol4007162,10.1002/ejoc.201201463,10.1021/ol303130j,10.1007/3418_2012_42,10.1021/op300236f,10.1016/j.tetlet.2012.08.015,10.1021/ol301847m,10.1021/ol301681z,10.1021/jo300713h,10.1016/j.tet.2012.04.005,10.1021/ol301275u,10.1021/ja210249h,10.1039/c2ob25425e,10.1002/chem.201103050,10.1039/c2sc20103hKelly11/9/20212011FALSEFALSEFALSEFALSE291766
430
459FALSEc1dt10858a10.1039/c1dt10858ahttps://sci-hub.wf/10.1039/c1dt10858ahttps://doi.org/10.1039/c1dt10858aNiC-H ActivationShihong17-MarTRUE421#N/A2011
10/24/2011Csp2-Csp2_arHXHIVinylArylNa2CO3Ionic-CO3Nu-H10.1016/j.trechm.2021.04.006,10.1002/adsc.202000820,10.1016/j.jorganchem.2019.05.019,10.1021/acs.chemrev.8b00514,10.1021/acs.chemrev.8b00505,10.1016/j.poly.2018.10.028,10.1016/j.poly.2018.08.007,10.1007/s11172-017-1920-7,10.1016/j.ccr.2017.03.007,10.1039/c7dt00643h,10.1016/j.jorganchem.2016.12.029,10.1021/acs.organomet.6b00532,10.1016/j.ica.2016.07.021,10.1515/chempap-2016-0036,10.1021/acs.organomet.6b00059,10.1039/c6ra02989b,10.1039/c6ra01918h,10.1039/c6dt00275g,10.1039/c5cy02235e,10.1002/anie.201505958,10.1016/j.jorganchem.2015.01.025,10.1016/j.ica.2014.11.005,10.1021/cs5014927,10.1039/c5dt02115d,10.1021/om500342z,10.6023/cjoc201307055,10.1039/c3dt52773e,10.1016/j.tetlet.2013.08.018,10.1016/j.crci.2013.01.016,10.1039/c3dt51777b,10.1039/c3ce40918j,10.1039/c3dt32835j,10.3762/bjoc.8.222,10.1016/j.tetlet.2012.07.107,10.1021/om300431r,10.1039/c2dt31739g3/24/2022
431
278FALSEc2cc33232a10.1039/c2cc33232ahttps://sci-hub.wf/10.1039/c2cc33232ahttps://doi.org/10.1039/c2cc33232aNiC-O ActivationShihong16-MarTRUE961012012Gong, HG
Nickel-catalyzed amination of aryl carbamates and sequential site-selective cross-couplings
CHEMICAL COMMUNICATIONS
We report the amination of aryl carbamates using nickel-catalysis. The methodology is broad in scope with respect to both coupling partners and delivers aminated products in synthetically useful yields. Computational studies provide the full catalytic cycle of this transformation, and suggest that reductive elimination is the rate-determining step. Given that carbamates are easy to prepare, robust, inert to Pdcatalysis, and useful for arene functionalization, these substrates are particularly attractive partners for use in synthesis. The sequential use of carbamate functionalization/site-selective cross-coupling processes highlights the utility of this methodology.
5/29/2012Csp2-Csp3E-EOXOCOPhI
Carbonyl
AlkylNo baseNo BaseStrong0.1310.1021/acscatal.9b00521,10.1039/c3ob40232k,10.1039/c5cc03113c,10.1021/acs.orglett.9b04497,10.1021/ol502682q,10.1021/acscatal.0c00246,10.1021/ol3013342,10.1002/anie.202002271,10.1021/ja510653n,10.1021/acs.orglett.9b0116410.1002/adsc.202200003,10.1002/anie.202114731,10.1002/anie.202112876,10.1039/d1qo01219c,10.1021/acscatal.1c02307,10.1021/acs.orglett.1c02874,10.1002/anie.202105354,10.1021/jacs.1c02629,10.1002/anie.202014660,10.1021/acs.orglett.0c03342,10.7536/PC200607,10.1021/acs.orglett.0c03210,10.1021/acs.orglett.0c02462,10.1021/acs.orglett.0c01869,10.1038/s41467-020-17224-2,10.1002/anie.202002271,10.1055/s-0039-1691525,10.1021/acs.orglett.0c00554,10.1248/cpb.c20-00075,10.1021/jacs.0c01475,10.1021/acs.orglett.0c00442,10.1021/acscatal.0c00246,10.1021/jacs.9b13920,10.1002/ejoc.201901865,10.1021/acs.orglett.9b04497,10.1021/acs.orglett.9b04320,10.1002/asia.201901490,10.1021/acs.orglett.9b02779,10.1002/chem.201903668,10.1021/acs.orglett.9b02788,10.1002/ijch.201900072,10.1016/j.tet.2019.06.034,10.1246/cl.190405,10.1002/anie.201906000,10.1039/c9cy00938h,10.1021/acs.orglett.9b01164,10.1021/jacs.9b02238,10.1021/acscatal.9b00521,10.6023/cjoc201806038,10.3390/catal9010053,10.1038/s41467-018-03532-1,10.1021/jacs.7b12212,10.1021/acs.orglett.7b03514,10.1016/bs.aihch.2017.10.001,10.1021/acs.orglett.7b01588,10.6023/cjoc201703042,10.6023/cjoc201610009,10.1021/acs.orglett.6b03158,10.1055/s-0035-1562442,10.1007/s41061-016-0042-2,10.6023/cjoc201602007,10.1021/acs.orglett.6b01134,10.1021/jacs.6b03897,10.1021/jacs.6b01533,10.1002/anie.201600697,10.1002/chem.201504985,10.1002/anie.201506432,10.1021/jacs.5b06255,10.5059/yukigoseikyokaishi.73.649,10.1021/acs.accounts.5b00057,10.1016/j.tet.2015.02.067,10.1039/c5ob01096a,10.1039/c5cc03113c,10.1039/c5qo00224a,10.1021/ja510653n,10.1002/chem.201405296,10.1021/ol502682q,10.1021/om5004682,10.1055/s-0033-1339126,10.1002/chem.201402509,10.1021/jo500507s,10.1002/chem.201402302,10.1055/s-0033-1340151,10.1080/00397911.2014.924141,10.1039/c4ra11520a,10.1055/s-0033-1338520,10.1021/ja407589e,10.1055/s-0033-1339435,10.1055/s-0033-1339297,10.1021/ja4030462,10.1021/ja402922w,10.1055/s-0032-1318237,10.1039/c3sc51098k,10.1039/c3ob40232k,10.1021/ol30133423/17/2022
432
466FALSEs-2005-86985410.1055/s-2005-869854https://sci-hub.wf/10.1055/s-2005-869854https://doi.org/10.1055/s-2005-869854NiC-H ActivationShihong22-MarTRUE102#N/A2005
6/17/2005Csp2-Csp2_arHXHIVinylArylNa2CO3Ionic-CO3Nu-H10.1021/acscatal.9b02230,10.1021/ja208450910.1002/slct.202001578,10.1016/j.tetlet.2019.151283,10.1021/acscatal.9b02230,10.1007/s11172-017-1920-7,10.3184/174751917X15040898434417,10.3184/174751917X15040898434417,10.1021/acs.organomet.6b00532,10.1039/c5cy02235e,10.1016/j.ica.2014.11.005,10.1021/cs5014927,10.1021/om500637k,10.1002/aoc.3134,10.1016/j.tetlet.2013.08.018,10.1021/om201101g,10.1021/ja2084509,10.1021/om200864z,10.1021/cr100198w,10.1055/s-0030-1258545,10.1016/S1872-2067(09)60089-9,10.1021/cr900074m,10.1002/adsc.200800662,10.1016/j.ccr.2007.03.011,10.1021/om700607m,10.1021/ja070321b,10.1002/anie.200603907,10.1016/j.tet.2006.05.006,10.1021/jo0608669,10.1021/om060043+3/24/2022
433
468FALSEanie.20150853610.1002/anie.201508536https://sci-hub.wf/10.1002/anie.201508536https://doi.org/10.1002/anie.201508536NiC-N ActivationKelly28-MarTRUE1153#N/A2015
11/16/2015Csp2-Osp2E-NuNH
N(Me)Ph
H
Carbonyl
ORNo baseNo Base10.1039/c7cc07457c,10.1002/chem.201602202,10.1055/s-0036-158884510.1002/anie.202200144,10.1021/acscatal.1c05738,10.1021/jacs.1c11898,10.1021/jacs.1c11898,10.1002/anie.202111029,10.1002/adsc.202101126,10.1039/d1ob01409a,10.1021/acs.chemrev.1c00225,10.1002/bkcs.12371,10.1021/acs.joc.1c01110,10.1002/anie.202104359,10.1016/j.tet.2021.132148,10.1039/d1dt00754h,10.1021/acs.joc.0c02929,10.1021/acs.orglett.0c03836,10.1021/acssuschemeng.0c08044,10.1021/acs.orglett.0c03953,10.1246/bcsj.20200182,10.1016/j.tetlet.2020.152444,10.1002/aoc.6073,10.3390/ph13100291,10.1021/acs.orglett.0c02457,10.1055/s-0040-1707101,10.3390/molecules25173959,10.1246/bcsj.20200071,10.1246/bcsj.20200116,10.1039/d0py00398k,10.1002/anie.202004272,10.1021/acs.joc.0c00227,10.1021/acscatal.9b05074,10.1002/adsc.202000122,10.1055/s-0039-1690055,10.1021/acs.orglett.0c00485,10.1007/s11426-019-9665-5,10.1038/s41467-020-14799-8,10.1021/acs.joc.9b02826,10.1039/c9sc03169c,10.1002/adsc.201901188,10.1021/acs.orglett.9b03274,10.1002/adsc.201900819,10.1021/acs.joc.9b02013,10.1021/acs.orglett.9b02862,10.1016/j.tet.2019.07.016,10.1021/jacs.9b04136,10.1002/ejoc.201900531,10.1021/acs.orglett.9b01053,10.1021/acs.orglett.9b00233,10.1021/acsomega.9b00081,10.1021/acs.orglett.8b03901,10.1016/j.jorganchem.2018.09.019,10.1002/anie.201810947,10.1055/s-0037-1610411,10.1021/acs.orglett.8b02911,10.1038/s41467-018-06623-1,10.1021/acscatal.8b02815,10.1021/acs.orglett.8b02323,10.1039/c8cs00201k,10.1021/acs.orglett.8b02006,10.1002/cctc.201800511,10.1038/s41467-018-05192-7,10.1039/c8qo00312b,10.1021/acs.orglett.8b01616,10.1002/ejoc.201800109,10.1007/s11426-017-9160-1,10.6023/A18020054,10.1021/acs.joc.8b00160,10.1016/j.tetlet.2018.01.097,10.1039/c7qo01031a,10.1002/chem.201800336,10.1021/acs.orglett.8b00086,10.1039/c7ob02874a,10.1021/acs.orglett.7b03943,10.1002/ejoc.201701527,10.1021/acscatal.7b02599,10.1021/acsomega.7b01540,10.1002/anie.201708665,10.1021/acs.orglett.7b03191,10.1039/c7cc07457c,10.1002/ejoc.201701060,10.1021/jacs.7b08813,10.1039/c7ob02269g,10.1039/c7sc03613b,10.1021/jacs.7b07344,10.1039/c7cs00182g,10.1002/anie.201707102,10.1021/acscatal.7b02540,10.1021/acs.orglett.7b02288,10.1039/c7cc04170e,10.1055/s-0036-1588845,10.1002/open.201700087,10.1002/chem.201702608,10.1002/asia.201700313,10.1021/acs.orglett.7b01575,10.1002/adsc.201700154,10.1002/chem.201605012,10.6023/cjoc201703024,10.1021/acs.joc.6b02093,10.1021/acs.joc.6b01080,10.1021/acscatal.6b02323,10.1002/chem.201604344,10.1055/s-0036-1588080,10.1021/acs.joc.6b01647,10.1002/chem.201603543,10.1021/acs.joc.6b01560,10.1002/chem.201602202,10.1038/srep28801,10.1002/anie.201601914,10.1021/acs.joc.6b00675,10.1021/acs.orglett.6b00842,10.1002/anie.201600919,10.1021/acs.orglett.6b00058,10.1039/c6ob00084c,10.1039/c6cc02324j4/4/2022
434
471FALSEanie.20211245410.1002/anie.202112454https://sci-hub.wf/10.1002/anie.202112454https://doi.org/10.1002/anie.202112454NiC-N ActivationKelly29-MarTRUE21#N/A
12/20/2021Csp3-ring(s)-Csp3NCsp2
Triphenylpyridinium+BF4-
CONHPIBenzylAlkylNo baseNo Base10.1002/anie.2021149104/4/2022
435
473FALSEacs.orglett.7b0119410.1021/acs.orglett.7b01194https://sci-hub.wf/10.1021/acs.orglett.7b01194https://doi.org/10.1021/acs.orglett.7b01194NiC-H ActivationKelly31-MarTRUE645#N/A2017
6/16/2017yCsp1-Csp2_arHCH
CON(CO)2(CH2)3
AlkyneArylNo baseNo BaseNu-Hxxx10.1021/jacs.7b09482,10.1021/acscatal.7b03688,10.1021/jacs.7b12865,10.1021/acs.orglett.9b04497,10.1021/acs.orglett.8b0102110.1039/d1sc06968c,10.1002/anie.202114146,10.1039/d1qo01539g,10.1039/d1qo00992c,10.1021/acs.joc.1c01110,10.1002/tcr.202100053,10.1021/acs.chemrev.0c00153,10.2174/1570179418666210224124931,10.1039/d0cc04960c,10.1055/s-0040-1705954,10.1021/acscatal.0c03334,10.1016/j.trechm.2020.08.001,10.1039/d0cc03309j,10.1021/acs.chemrev.9b00682,10.1021/acs.joc.0c00227,10.1016/j.tetlet.2020.151647,10.1002/asia.202000117,10.1021/acs.orglett.9b04497,10.1021/acs.joc.9b02826,10.1039/c9cc08663c,10.1021/acs.orglett.9b03434,10.1039/c9cc07558e,10.1002/chem.201904842,10.1177/1747519819873514,10.1039/c9cc05763c,10.1039/c9qo00489k,10.1002/ejoc.201900531,10.1039/c9qo00106a,10.1021/acs.orglett.8b03901,10.1002/asia.201801317,10.1039/c8ob01832d,10.1039/c8cs00335a,10.1021/acs.orglett.8b02911,10.1039/c8qo00591e,10.1021/acscatal.8b02815,10.3390/molecules23102681,10.1039/c8ob01389f,10.1002/asia.201800478,10.1039/c8cc03954b,10.1002/cctc.201800511,10.1002/ejoc.201800109,10.1002/chem.201704670,10.1021/acs.orglett.8b01021,10.1021/acs.orglett.8b01233,10.1021/acs.orglett.8b00949,10.1016/j.tetlet.2018.01.097,10.1021/jacs.7b12865,10.1002/chem.201705842,10.1002/chem.201800336,10.1021/acs.orglett.8b00086,10.1039/c7ob02874a,10.1039/c8cc00271a,10.1021/acs.orglett.8b00080,10.1021/acscatal.7b03688,10.1055/s-0036-1591495,10.1039/c7ob02269g,10.1021/jacs.7b09482,10.1002/anie.201707102,10.1021/acscatal.7b02540,10.1002/chem.201702867,10.1021/acs.orglett.7b01905,10.1021/acs.orglett.7b015754/4/2022
436
103FALSEc3981000031310.1039/c39810000313https://sci-hub.wf/10.1039/c39810000313https://doi.org/10.1039/c39810000313NiC-O ActivationShihong7-FebTRUE522681981Kumada , M
Mild ketone formation via Ni-catalyzed reductive coupling of unactivated alkyl halides with acid anhydrides
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
Ni-catalyzed ketone formation through mild reductive coupling of a diverse set of unactivated alkyl bromides and iodides with particularly aryl acid anhydrides was successfully developed using zinc as the terminal reductant. These conditions also allow direct coupling of alkyl iodides with aryl acids in the presence of Boc(2)O and MgCl2.
01/1/1981Csp3-Csp2_arE-NuOMgOSiEt3MgXAllylArylNo baseNo BaseStrong-0.27_10.1039/c7sc03140h,10.1039/c3983000011210.1002/anie.202008071,10.1002/anie.201905021,10.1021/jacs.8b10766,10.1055/S-0036-1591774,10.1039/c7sc03140h,10.1039/c4qo00097h,10.1002/chem.201202824,10.1007/3418_2011_14,10.1007/3418_2011_15,10.1021/ol2012007,10.1002/anie.201008174,10.1055/s-0029-1218756,10.1016/j.tet.2008.11.007,10.1002/ejic.200601051,10.1246/cl.2007.236,10.1139/V05-085,10.1016/j.tet.2005.02.026,10.1002/adsc.200404192,10.1021/ol0340641,10.1021/jo026421b,10.1021/ol000038g,10.1021/jo981130h,10.1246/cl.1998.1053,10.1021/ic00130a006,10.1080/00397919508015850,10.1016/0304-5102(93)85084-7,10.3891/acta.chem.scand.47-0196,10.1016/S0957-4166(00)82091-1,10.1016/S0065-3055(08)60016-7,10.1021/cr00091a007,10.1016/0022-328X(88)80540-0,10.1016/0022-328X(87)87187-5,10.1021/ja00255a017,10.1021/om00153a013,10.1021/om00146a015,10.1007/BF00959380,10.1016/0022-328X(86)80547-2,10.1021/ja00312a071,10.1021/om00127a020,10.1021/om00128a003,10.1007/BF00960306,10.1246/bcsj.57.480,10.1021/jo00196a043,10.1021/ja00313a032,10.1039/c39840000968,10.1016/S0022-328X(00)99425-7,10.1039/c39830000112checked by Kelly1/25/2022
437
130FALSEc3983000011210.1039/c39830000112https://sci-hub.wf/10.1039/c39830000112https://doi.org/10.1039/c39830000112NiC-O ActivationLong16-FebTRUE633431983
CONSIGLIO, G
REGIOSELECTIVE ALLYLATION OF A GRIGNARD-REAGENT CATALYZED BY PHOSPHINE-NICKEL AND PHOSPHINE-PALLADIUM COMPLEXES
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
SWISS FED INST TECHNOL,DEPT IND & ENGN CHEM,CH-8092 ZURICH,SWITZERLAND.
1/1/1983Csp3-Csp2_arE-NuOMgOPhMgXAlkylArylNo baseNo BaseStrong-0.32_10.1021/ja00132a039,10.1021/ol5016724,10.1016/S0040-4020(01)87621-310.1002/ejic.202100820,10.6023/cjoc202106021,10.1039/c9cc09899b,10.1021/acs.orglett.9b03633,10.6023/cjoc201809037,10.1002/cjoc.201800237,10.1002/ajoc.201800094,10.1021/acs.chemrev.5b00162,10.1021/ol5016724,10.1007/3418_2011_14,10.1002/chem.200801879,10.1021/ja800103z,10.1016/S0040-4020(97)10212-5,10.1016/S0040-4039(97)00178-0,10.1021/ja00132a039,10.1021/om00018a016,10.1016/0304-5102(93)85091-7,10.1016/0022-328X(91)80189-Q,10.1021/om00162a014,10.1016/0304-5102(90)85092-V,10.1016/S0040-4039(00)94338-7,10.1016/0022-328X(89)87299-7,10.1021/ic00301a012,10.1021/cr00091a007,10.1039/dt9890000161,10.1016/S0040-4020(01)89159-6,10.1021/jo00253a049,10.1021/ja00226a067,10.1021/jo00236a023,10.1016/S0040-4020(01)86035-X,10.1016/0010-8545(87)80017-6,10.1021/ja00255a017,10.1021/jo00390a013,10.1021/ja00239a029,10.1016/S0020-1693(00)88365-6,10.1246/cl.1987.1373,10.1016/S0040-4020(01)87666-3,10.1021/jo00376a022,10.5059/yukigoseikyokaishi.44.499,10.1016/S0040-4020(01)87621-3,10.1016/S0040-4020(01)82073-1,10.1016/S0040-4039(00)83974-X,10.1021/ja00312a071,10.1021/jo00210a051,10.1021/jo00218a004,10.1016/0022-328X(85)80323-5,10.1016/0022-328X(85)80001-2,10.1021/ja00293a038,10.1021/om00126a012,10.1016/S0040-4039(00)98166-8,10.1016/S0040-4039(00)98674-X,10.1002/anie.198407821,10.1021/ja00334a060,10.1039/c39840000309,10.1039/c39830001215,10.1039/dt9830002293,10.1351/pac198355111781Kelly2/17/2022
438
478FALSEjacs.1c1093210.1021/jacs.1c10932https://sci-hub.wf/10.1021/jacs.1c10932https://doi.org/10.1021/jacs.1c10932NiC-N ActivationLong6-AprTRUE41#N/A2021
12/15/2021Csp3-ring(s)-Csp2_arE-ENX
Triphenylpyridinium+BF4-
IBenzylArylTMENitrogenNitrogen(neutral)10.1002/chem.202102347,10.1021/acs.joc.1c01073,10.1021/acscatal.1c01860,10.1039/d1sc00943e,10.1021/jacs.0c13093,10.1021/jacs.0c11172,10.1021/acscatal.0c03237,10.1021/acscatal.0c01842,10.1021/jacs.0c05254,10.1021/jacs.0c04812,10.1021/acs.oprd.0c00134,10.1002/anie.202002271,10.1021/jacs.0c02673,10.1021/acscatal.0c01199,10.1002/anie.201915412,10.1021/jacs.0c02805,10.1021/acs.orglett.0c00554,10.1002/anie.201915418,10.1021/jacs.0c01475,10.1021/acs.orglett.0c00442,10.1021/jacs.0c01330,10.1007/s41981-019-00050-z,10.1055/s-0039-1690703,10.1021/acs.orglett.9b04117,10.1039/c9cc08348k,10.1038/s41557-019-0353-3,10.1002/anie.201912753,10.1021/jacs.9b10026,10.1021/jacs.9b04510,10.1021/acscatal.9b03352,10.1021/jacs.9b02973,10.1246/cl.190403,10.1021/acscatal.9b01785,10.1021/acs.oprd.9b00232,10.1038/s41929-019-0292-9,10.1039/c9cc00768g,10.1002/anie.201809431,10.1021/acs.orglett.9b01097,10.1039/c9sc00783k,10.1021/jacs.9b02238,10.1021/acs.orglett.9b01014,10.1021/acs.orglett.9b01016,10.1021/acscatal.9b00566,10.1002/anie.201900228,10.1126/science.aau0364,10.1021/acs.orglett.8b04090,10.1039/c8sc04437f,10.1126/science.aac6153,10.1039/c8sc04335c,10.1021/jacs.8b12025,10.1002/anie.201803186,10.1021/acscatal.8b03437,10.1038/s41467-018-07198-7,10.1021/jacs.8b08605,10.1002/anie.201809310,10.1021/acs.oprd.8b00237,10.1021/jacs.8b05868,10.1021/acsmedchemlett.8b00183,10.1038/s41467-018-04646-2,10.1021/acs.orglett.8b01062,10.1038/s41586-018-0056-8,10.1021/acs.orglett.8b00413,10.1038/s41467-018-03532-1,10.1021/acs.orglett.8b00070,10.1055/s-0036-1591853,10.1126/science.aap9112,10.1021/acscatal.7b03388,10.1021/acs.chemrev.7b00183,10.1021/jacs.7b05901,10.1021/acs.joc.7b01334,10.1021/acs.orglett.7b01598,10.1021/jacs.7b03195,10.1021/jacs.7b03448,10.1021/acs.orglett.7b00793,10.1002/ejoc.201601571,10.1002/aic.15642,10.1021/acs.joc.6b02830,10.1002/anie.201609662,10.1021/acs.oprd.6b00370,10.1002/anie.201607959,10.1038/NCHEM.2587,10.1021/acs.orglett.6b01837,10.1002/chem.201602668,10.1021/jacs.6b04818,10.1021/acs.orglett.6b01134,10.1002/anie.201601206,10.1021/jacs.6b01533,10.1021/acs.oprd.6b00015,10.1039/c5sc04751j,10.1039/c5gc01008j,10.1002/anie.201507902,10.1021/jacs.5b06255,10.1021/jacs.5b06466,10.1002/anie.201503936,10.1021/acs.accounts.5b00057,10.1126/science.aab0245,10.1126/science.aaa5414,10.1126/science.1259203,10.1039/c5qo00224a,10.1039/c4sc03106g,10.1021/ja510653n,10.1021/ja508067c,10.1021/ol501495d,10.1002/chem.201402509,10.1021/jo500507s,10.1002/chem.201402302,10.1002/anie.201209060,10.1021/ja407589e,10.1016/j.drudis.2013.03.001,10.1021/ol400295z,10.1021/ja3089422,10.1021/op200348t,10.1021/ja301769r,10.1021/jm200187y,10.1039/c0gc00797h,10.1021/ja9093956,10.1002/anie.200703883,10.1002/anie.200400654,10.1002/1521-3773(20001117)39:22<4036::AID-ANIE4036>3.0.CO;2-L,10.1016/S0040-4039(99)02006-7,10.1039/a703610h,10.1002/anie.199610111,10.1016/0040-4039(96)00290-0,10.1021/jo00123a034,10.1016/0040-4039(95)00386-Q,10.1021/jo00274a0194/15/2022
439
480FALSEjacs.8b1325110.1021/jacs.8b13251https://sci-hub.wf/10.1021/jacs.8b13251https://doi.org/10.1021/jacs.8b13251NiC-H ActivationLong8-AprTRUE891#N/A2019
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NICKEL CATALYZED ASYMMETRIC COUPLING REACTION BETWEEN ALLYL PHENYL ETHERS AND GRIGNARD-REAGENTS
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
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446
488FALSEa702954c10.1039/a702954chttps://sci-hub.wf/10.1039/a702954chttps://doi.org/10.1039/a702954cNiC-N Activation12-MayFALSE281#N/A1997#N/A#N/A
447
273FALSEc3995000186310.1039/c39950001863https://sci-hub.wf/10.1039/c39950001863https://doi.org/10.1039/c39950001863NiC-O ActivationGerry14-MarTRUE502381995MORTREUX, A
NICKEL-CATALYZED SUBSTITUTION-REACTIONS OF ALLYLIC CARBONATES WITH ARYL-BORATES AND ALKENYL-BORATES
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
Substitution reactions of 1,3-disubstituted allylic carbonates 3 with aryl- and alkenyl-borates 4 are catalysed by [NiCl2(dppf)][dppf = 1,1'-bis(diphenylphosphino)ferrocene], and in the case of the cyclic carbonate 7, the reaction proceeds with complete inversion.
9/21/1995Csp3-Nsp3E-NuOHOAcHAllyl
N(Alkyl)Alkyl
No baseNo BaseMedium0.31_10.1016/0040-4039(96)01302-0,10.1002/anie.20170348610.1002/ejic.202100820,10.1055/a-1657-5543,10.1021/acscatal.1c03449,10.1039/d0qo01087a,10.1021/acs.chemrev.9b00682,10.1021/acs.orglett.0c01109,10.6023/cjoc201809037,10.1021/acs.organomet.8b00438,10.1002/anie.201703486,10.1002/adsc.201100809,10.1007/3418_2011_15,10.1007/978-3-642-15334-1_7,10.1016/j.tetlet.2009.12.036,10.1016/j.tet.2009.12.004,10.1016/j.tet.2009.04.005,10.1021/jo800155a,10.1002/ejoc.200800007,10.1107/S1600536805005064,10.1016/j.tetasy.2004.06.052,10.1080/02603590390464216,10.1055/s-2002-35576,10.2174/1385272023373545,10.1021/jo020281o,10.1002/1521-3773(20020503)41:9<1603::AID-ANIE1603>3.0.CO;2-D,10.1021/om010343l,10.1021/ja0112036,10.1021/jo0006268,10.1016/S0040-4039(00)01448-9,10.1021/cr9902749,10.1021/om990533k,10.1021/ja991704f,10.1002/(SICI)1521-3773(19991102)38:21<3163::AID-ANIE3163>3.0.CO;2-#,10.1016/S1381-1169(98)00067-3,10.1021/ja981560p,10.1021/jo980200h,10.1039/a802876a,10.1021/ja980030q,10.1016/S0040-4039(98)00142-7,10.1016/S0040-4020(97)10208-3,10.1039/a702954c,10.1016/S0010-8545(97)90135-1,10.1016/S0040-4039(96)02510-5,10.1016/0040-4039(96)01302-0,10.1039/co9960300277,10.1016/S0022-328X(96)06161-X3/14/2022
448
112FALSEc3cc46663a10.1039/c3cc46663ahttps://sci-hub.wf/10.1039/c3cc46663ahttps://doi.org/10.1039/c3cc46663aNiC-O ActivationKellyTRUE573332013Tu, T
NICKEL-CATALYZED SUBSTITUTION-REACTIONS OF ALLYLIC COMPOUNDS WITH SOFT NUCLEOPHILES - AN EFFICIENT ALTERNATIVE TO PALLADIUM CATALYSIS
CHEMICAL COMMUNICATIONS
Substitution reactions of allyl alcohol derivatives la-e with diethylamine, phenol and dimethyl malonate are efficiently carried out in the presence of Ni(dppb)(2) (dppb = 1,2-diphenylphosphinobutane) as catalyst and ammonium salts or bases as-promoters or co-reagents.
Fudan Univ10/17/2013TRUEFALSEFALSECsp2_ar-Csp2_arE-NuOBOPivB(OH)2ArylArylK3PO4Ionic-PO4Medium0.33_xx10.1021/acs.joc.6b01627,10.1021/acs.orglett.6b01398,10.1021/jo501291y10.1039/d1ob00955a,10.1039/d0dt03593a,10.1134/S1023193521020075,10.1055/a-1349-3543,10.24820/ark.5550190.p011.533,10.1002/aoc.6012,10.1021/acs.chemrev.0c00088,10.1021/acs.organomet.9b00834,10.1021/acs.joc.9b03077,10.1016/j.ica.2020.119457,10.1002/slct.201904819,10.1021/acs.jpca.9b00846,10.1002/ejic.201801179,10.1007/3418_2018_19,10.1002/asia.201800759,10.1002/adsc.201800729,10.1002/cctc.201702019,10.1021/acs.organomet.7b00848,10.1016/j.catcom.2017.09.021,10.1021/acs.organomet.7b00692,10.1002/asia.201701303,10.1002/asia.201700877,10.1007/s11172-017-1920-7,10.1021/acsomega.7b00725,10.1016/j.ccr.2017.03.007,10.1021/acscatal.6b02912,10.1039/c6nj03789e,10.1002/anie.201611162,10.1016/j.cclet.2016.09.006,10.1039/c6dt03944h,10.1021/acs.joc.6b01627,10.1002/slct.201600978,10.1007/s41061-016-0043-1,10.1021/acs.orglett.6b01398,10.1016/j.ccr.2015.11.010,10.1016/bs.adomc.2016.07.001,10.1007/3418_2015_127,10.1039/c5dt04429d,10.1016/j.tet.2015.02.088,10.1016/j.ica.2014.11.005,10.1021/cs5014927,10.1039/c5qo00236b,10.1039/c4cy01736f,10.1039/C5CC00196J,10.1021/jo501291y,10.1039/c4qo00233d,10.1039/c4qo00253a,10.1071/CH14171,10.1039/c4cc04743e,10.1039/c4dt00461bKelly12/15/20212013FALSEFALSEFALSEFALSE499811539
449
67FALSEc3ob40232k10.1039/c3ob40232khttps://sci-hub.wf/10.1039/c3ob40232khttps://doi.org/10.1039/c3ob40232kNiC-O ActivationGerryTRUE425172013Qian, Q
Suzuki-Miyaura cross-coupling of bulky anthracenyl carboxylates by using pincer nickel N-heterocyclic carbene complexes: an efficient protocol to access fluorescent anthracene derivatives
ORGANIC & BIOMOLECULAR CHEMISTRY
A series of fluorescent (hetero)-aryl substituted anthracene derivatives were readily accessible from the corresponding bulky anthracen-9-yl carboxylates via Suzuki-Miyaura cross-coupling reactions by using pincer nickel N-heterocyclic carbene complex 1 even at the catalyst loading as low as 0.1 mol% in the presence of catalytic amounts of PCy3.
Shanghai Univ4/2/2013yCsp3-Csp2_arE-EOXOAcBrAllylArylNitrogenNitrogen(neutral)Medium0.31_10.1039/c7sc03140h,10.1002/anie.201601206,10.1039/c5cc03113c,10.1021/jacs.0c13093,10.1055/s-0037-161008410.1055/s-0041-1737762,10.1002/chem.202103643,10.1039/d1sc02547c,10.1021/acs.orglett.1c00812,10.6023/cjoc202008012,10.1021/jacs.0c13093,10.1021/acs.orglett.0c03865,10.1039/d0cc05895e,10.1021/acscatal.0c02454,10.1002/anie.201915454,10.1021/acs.orglett.9b02473,10.1021/acs.orglett.9b01987,10.1039/c9cc03737c,10.1021/acs.orglett.9b01019,10.1002/anie.201805118,10.1055/s-0037-1610084,10.1002/anie.201803228,10.1055/s-0036-1591853,10.1039/c7sc03140h,10.1002/cjoc.201700071,10.1126/science.aan1568,10.1002/anie.201703174,10.1002/chem.201603832,10.1038/NCHEM.2587,10.1007/s41061-016-0042-2,10.1002/chem.201601515,10.1021/acs.orglett.6b01134,10.1002/anie.201601206,10.1002/ejoc.201501551,10.1055/s-0035-1560531,10.1055/s-0034-1381034,10.1039/c5cc03113c,10.1039/c5qo00224a,10.1016/j.tet.2014.10.061,10.1021/ja508067c,10.1002/chem.2014023021/19/2022
450
96FALSEc4cc08187k10.1039/c4cc08187khttps://sci-hub.wf/10.1039/c4cc08187khttps://doi.org/10.1039/c4cc08187kNiC-O ActivationGerryTRUE5111892015Rueping, M
Nickel-catalyzed reductive allylation of aryl bromides with allylic acetates
CHEMICAL COMMUNICATIONS
This paper highlights Ni-catalyzed allylation of electron-rich aryl bromides with a variety of substituted allylic carbonates using zinc as the terminal reductant, affording E-alkenes regioselectively in good to excellent yields by the addition of aryl to the less hindered allylic carbon. The electron-deficient aryl bromides and chlorides are also highly efficient coupling partners.
Rhein Westfal TH Aachen
12/22/2014Csp2-Csp3E-NuOLiOMeLiVinyl
Csp3-Si
No baseNo BaseStrong-0.28_xx10.1021/acscatal.6b00801,10.1002/chem.201505106,10.1002/chem.201702867,10.1002/anie.201607646,10.1002/anie.201510497,10.1021/acscatal.7b01058,10.1021/acs.orglett.7b00556,10.1002/chem.201603436,10.1246/cl.150936,10.1021/acscatal.7b00941,10.1021/acs.orglett.5b0220010.1039/d1qo00549a,10.1039/d0cc05271j,10.1039/c9qo01428d,10.1002/chem.201904842,10.1021/acs.orglett.9b02572,10.1246/cl.190393,10.1002/cjoc.201800554,10.1002/adsc.201801713,10.1021/acs.orglett.9b00394,10.1016/j.tetlet.2018.11.026,10.1016/j.tet.2018.10.033,10.1002/anie.201809003,10.1021/jacs.8b08596,10.1039/c8cc03665a,10.1002/anie.201806237,10.1002/chem.201704670,10.1021/acs.accounts.8b00023,10.1055/s-0036-1591495,10.1002/anie.201707309,10.1002/chem.201702867,10.1248/cpb.c17-00487,10.1021/acs.orglett.7b01905,10.1021/acscatal.7b00941,10.1021/acscatal.7b01058,10.1039/c7cc00078b,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1002/anie.201612624,10.1021/acs.orglett.6b03861,10.1002/anie.201607646,10.1021/jacs.6b10255,10.1002/chem.201604452,10.1002/chem.201604504,10.1246/cl.160712,10.1002/chem.201603436,10.1002/anie.201604696,10.1021/acscatal.6b00801,10.1002/anie.201510497,10.1002/chem.201505106,10.1055/s-0035-1560380,10.1016/bs.adomc.2016.07.001,10.1039/c6ob01765g,10.1246/cl.150936,10.1002/chem.201502114,10.1021/acs.orglett.5b02200,10.1021/acs.joc.5b01216,10.1021/acs.orglett.5b00905,10.1039/c5qo00001g1/10/2022
451
146FALSEc4cc08426h10.1039/c4cc08426hhttps://sci-hub.wf/10.1039/c4cc08426hhttps://doi.org/10.1039/c4cc08426hNiC-O ActivationLongTRUE776492015Yamaguchi, J
Nickel catalyzed dealkoxylative C-sp2-C-sp3 cross coupling reactions - stereospecific synthesis of allylsilanes from enol ethers
CHEMICAL COMMUNICATIONS
The application of cyclic and acyclic enol ethers as electrophiles in cross coupling reactions offers new possibilities for the preparation of functional compounds. A novel nickel catalyzed dealkoxylative cross coupling reaction allows access to structurally diverse allylsilanes and alcohol derivatives with high stereospecificity and in good yields under mild reaction conditions directly from the corresponding enol ethers.
Nagoya Univ11/21/2014Csp2_ar-Csp3E-NuOH
OCONMe2
HArylAllylK3PO4Ionic-PO4Medium0.31_x10.1021/acs.orglett.6b02265,10.1021/acscatal.0c00291,10.1021/acscatal.6b00801,10.1039/c5sc02942b,10.1021/jacs.7b04973,10.1021/acs.orglett.6b0265610.1039/d2ob00003b,10.1039/d1ob02349g,10.1021/acs.joc.1c02435,10.1016/j.jorganchem.2021.121925,10.1021/jacs.1c04215,10.21577/0103-5053.20200192,10.1021/acs.joc.0c00999,10.1002/adsc.202000794,10.1021/acs.organomet.0c00573,10.1055/s-0040-1705943,10.1021/acs.chemrev.0c00088,10.1002/ejoc.202001057,10.1021/acs.chemrev.9b00682,10.1002/cjoc.201900506,10.1021/acscatal.0c00291,10.1021/acscatal.9b04212,10.1002/adsc.201900819,10.1021/acs.organomet.9b00340,10.1002/ejic.201801570,10.1002/anie.201814475,10.1039/c8sc05170d,10.1007/3418_2018_19,10.1002/asia.201800478,10.1021/acs.oprd.8b00182,10.1021/acs.joc.8b00264,10.1039/c8ob01034j,10.1002/ajoc.201800207,10.1246/cl.180226,10.1016/j.jorganchem.2018.01.019,10.1021/acs.orglett.8b01233,10.1021/acs.orglett.8b00080,10.1039/c7cc08709h,10.1055/s-0036-1589120,10.1021/acs.joc.7b02423,10.1039/c7cs00182g,10.1021/jacs.7b04973,10.1021/acs.joc.7b00855,10.1002/bkcs.11127,10.1016/j.tet.2017.02.021,10.1246/bcsj.20160365,10.1002/adsc.201601302,10.1021/jacs.7b00049,10.1246/cl.161001,10.1021/acscatal.6b02964,10.1021/acs.orglett.6b02656,10.1021/acs.orglett.6b02556,10.1016/j.tetlet.2016.08.017,10.1021/acs.orglett.6b02265,10.1021/acs.orglett.6b02094,10.1002/chem.201602150,10.1007/s41061-016-0043-1,10.1055/s-0035-1561859,10.1021/acscatal.6b00801,10.1246/cl.160133,10.1002/chem.201504959,10.1002/adsc.201500822,10.1021/acscatal.5b02058,10.1016/bs.adomc.2016.07.001,10.1039/c6cc00971a,10.1039/c5cc10005d,10.1055/s-0035-1560726,10.1039/c6ra07130a,10.1002/chem.201503414,10.1021/acs.organomet.5b00733,10.1002/anie.201503204,10.1016/j.tet.2015.02.088,10.1021/jacs.5b04548,10.1021/acs.accounts.5b00051,10.1039/c5sc02942b,10.1039/c5cc05506g,10.1039/c5sc00305a,10.1039/c5cy00851dKelly12/10/2021
452
494FALSEacs.orglett.7b0098910.1021/acs.orglett.7b00989https://sci-hub.wf/10.1021/acs.orglett.7b00989https://doi.org/10.1021/acs.orglett.7b00989NiC-N ActivationxJustin29-MayFALSE951#N/A2017#N/A#N/A
453
495FALSEjacs.6b0839710.1021/jacs.6b08397https://sci-hub.wf/10.1021/jacs.6b08397https://doi.org/10.1021/jacs.6b08397NiC-H ActivationxWilliam29-MayTRUE841#N/A2016
YCsp3-Csp2_arHXHClAlkylArylK3PO4Ionic-PO4Nu-H6/1/2022
454
496FALSEacscatal.1c0285110.1021/acscatal.1c02851https://sci-hub.wf/10.1021/acscatal.1c02851https://doi.org/10.1021/acscatal.1c02851NiC-H ActivationxWilliam29-MayTRUE181#N/A2021
YCsp3-ring(s)-Csp2HXHBrBenzylVinylK2HPO4Nu-H6/1/2022
455
497FALSEjacs.7b0707810.1021/jacs.7b07078https://sci-hub.wf/10.1021/jacs.7b07078https://doi.org/10.1021/jacs.7b07078NiC-H ActivationxWilliam29-MayTRUE1031#N/A2017
Triple catalytic system (H+)yCsp2-Csp2_arHXHBr
Carbonyl
ArylK2CO3Ionic-CO3Nu-H6/1/2022
456
498FALSEjacs.8b0740510.1021/jacs.8b07405https://sci-hub.wf/10.1021/jacs.8b07405https://doi.org/10.1021/jacs.8b07405NiC-H ActivationxWilliam29-MayTRUE591#N/A2018
YCsp3-Csp2_arHXHBrAlkylArylNa2CO3Ionic-CO3Nu-H6/1/2022
457
499FALSEc6sc02815b10.1039/c6sc02815bhttps://sci-hub.wf/10.1039/c6sc02815bhttps://doi.org/10.1039/c6sc02815bNiC-H ActivationxWilliam29-MayTRUE1031#N/A2016
YCsp3-Csp2_arHXHIAlkylArylKOHIonic-ORNu-H6/1/2022
458
500FALSEanie.20190132710.1002/anie.201901327https://sci-hub.wf/10.1002/anie.201901327https://doi.org/10.1002/anie.201901327NiC-H ActivationxWilliam29-MayTRUE831#N/A2019
YCsp3-ring(s)-Csp2_arHXHBrBenzylArylK2HPO4Nu-H6/1/2022
459
501FALSEanie.20181052610.1002/anie.201810526https://sci-hub.wf/10.1002/anie.201810526https://doi.org/10.1002/anie.201810526NiC-H ActivationxWilliam29-MayTRUE591#N/A2019
Csp3-Csp3HXHBrAlkylAlkylK2HPO4Nu-H6/1/2022
460
281FALSEc4sc03106g10.1039/c4sc03106ghttps://sci-hub.wf/10.1039/c4sc03106ghttps://doi.org/10.1039/c4sc03106gNiC-O ActivationLong5-AprTRUE1381382015Weix, DJ
Ni-Catalyzed alpha-arylation of esters and amides with phenol derivatives
CHEMICAL SCIENCE
A nickel-catalyzed alpha-arylation of esters and amides with phenol derivatives has been accomplished. In the presence of our unique nickel catalyst, prepared in situ from Ni(cod)(2), 3,4-bis(dicyclohexyl-phosphino) thiophene (dcypt), and K3PO4, various esters and amides undergo alpha-arylation with O-arylpivalates or O-arylcarbamates to afford the corresponding coupling products. The thus obtained alpha-aryl esters and amides are useful precursors of privileged motifs such as alpha-arylcarboxylic acids and beta-arylamines.
11/10/2014Csp3-ring(s)-Csp2_arE-EOX
OP(O)(OEt)2
BrBenzylArylNo baseNo BaseStrong0.0410.1021/acs.orglett.2c00355,10.1002/anie.202115702,10.1002/anie.202112533,10.1021/acscatal.1c05586,10.1055/s-0041-1737762,10.1021/acs.orglett.1c03991,10.1021/acscatal.1c05208,10.1021/jacs.1c10932,10.1021/acscatal.1c04239,10.6023/cjoc202106021,10.1039/d1ob01874d,10.1039/d1sc04011a,10.1021/acs.orglett.1c02096,10.1002/chem.202102347,10.1021/jacs.1c05764,10.1021/acs.orglett.1c02114,10.1142/S1088424621500528,10.1021/jacs.1c00659,10.1021/jacs.1c03527,10.1055/a-1467-2432,10.1002/anie.202101682,10.1021/jacs.0c13093,10.1002/chem.202100075,10.1038/s41467-020-20888-5,10.1021/jacs.0c12462,10.1021/jacs.0c12843,10.1007/s11426-020-9910-2,10.1055/s-0040-1707342,10.1055/s-0040-1707216,10.1021/acscatal.0c03237,10.1021/acscatal.0c03903,10.1021/acsomega.0c04181,10.1002/adsc.202000945,10.1002/anie.202010386,10.1021/acscatal.0c01842,10.1021/acs.joc.0c01274,10.1002/anie.202003948,10.1002/aoc.5741,10.1021/acs.organomet.0c00021,10.1021/acs.orglett.0c00688,10.1016/j.tetlet.2020.151729,10.1021/jacs.0c01330,10.1021/jacs.0c00245,10.1002/ejoc.201901137,10.1021/acs.orglett.9b04117,10.1002/anie.201903726,10.1002/anie.201912753,10.1002/anie.201913743,10.1021/acs.joc.9b02554,10.1002/chem.201905048,10.1002/ajoc.201900625,10.1016/j.trechm.2019.08.004,10.1039/c9qo00747d,10.1039/c9sc03347e,10.1016/j.tetlet.2019.150991,10.1038/s41467-019-11392-6,10.1021/acs.orglett.9b01987,10.1002/ejoc.201900465,10.1039/c9ob00628a,10.1021/acs.orglett.9b00692,10.1021/acscatal.9b00521,10.1021/acs.orglett.9b00174,10.1002/ejoc.201801888,10.1021/jacs.8b13524,10.6023/cjoc201806038,10.1002/anie.201811343,10.1021/jacs.8b12634,10.1021/acs.organomet.8b00720,10.1002/cjoc.201800500,10.1021/acs.orglett.8b03367,10.1039/c8qo01044g,10.1021/acscatal.8b03930,10.1021/acs.orglett.8b02498,10.1021/jacs.8b05143,10.1021/acscatal.8b02784,10.1021/jacs.8b06458,10.1021/jacs.8b05743,10.1055/s-0037-1610084,10.1021/acs.orglett.8b01863,10.1039/c8cc02380h,10.1039/c8sc00609a,10.1002/cctc.201701601,10.1021/acscatal.8b00244,10.1021/acs.organomet.7b00894,10.1002/anie.201712428,10.1021/acs.orglett.8b00235,10.1055/s-0037-1609093,10.1039/c7np00065k,10.1039/c7sc03404k,10.1039/c7sc03140h,10.1021/jacs.7b11707,10.2174/1385272822666181010125902,10.1021/acs.orglett.7b03049,10.1039/c7ob02007d,10.1021/jacs.7b08064,10.1038/s41570-017-0065,10.1039/c7cc01932g,10.1021/acs.orglett.7b00831,10.1021/jacs.7b01705,10.1039/c6sc90082h,10.1002/chem.201603832,10.1021/acs.orglett.6b02862,10.1021/jacs.6b08507,10.1055/s-0035-1562442,10.1021/acs.orglett.6b01675,10.1021/acs.orglett.6b01837,10.1002/chem.201602668,10.1007/s41061-016-0042-2,10.1002/adsc.201600378,10.1002/anie.201603627,10.1021/acs.orglett.6b01134,10.1002/anie.201601206,10.1002/chem.201601320,10.1021/jacs.6b01533,10.1002/anie.201600697,10.1021/acs.joc.5b02441,10.1002/anie.201507902,10.1021/jacs.5b06466,10.1002/anie.201503936,10.1021/jacs.5b03870,10.1021/acs.accounts.5b00057,10.1021/acs.joc.5b00135,10.1039/c5ob01096a,10.1039/c5cc03113c,10.1039/c5sc90021b,10.1039/c5qo00224a4/15/2022
461
262FALSEc5cc03113c10.1039/c5cc03113chttps://sci-hub.wf/10.1039/c5cc03113chttps://doi.org/10.1039/c5cc03113cNiC-O ActivationGerry5-MarTRUE54312015Gong, HG
Cobalt co-catalysis for cross-electrophile coupling: diarylmethanes from benzyl mesylates and aryl halides
CHEMICAL COMMUNICATIONS
The nickel-catalyzed cross-coupling of aryl halides with alkyl radicals derived from alkyl halides has recently been extended to couplings with carbon radicals generated by a co-catalyst. In this study, a new co-catalyst, cobalt phthalocyanine (Co(Pc)), is introduced and demonstrated to be effective for coupling substrates not prone to homolysis. This is because Co(Pc) reacts with electrophiles by an S(N)2 mechanism instead of by the electron-transfer or halogen abstraction mechanisms previously explored. Studies demonstrating the orthogonal reactivity of (bpy)Ni and Co(Pc), applying this selectivity to the coupling of benzyl mesylates with aryl halides, and the adaptation of these conditions to the less reactive benzyl phosphate ester and an enantioconvergent reaction are presented.
5/14/2015Csp2-Csp3E-EOXOHBr
Carbonyl
Alkyl#N/ANo BaseStrong-0.81_10.1021/acs.orglett.9b04497,10.1002/anie.202002271,10.1021/acs.orglett.9b0116410.1002/adsc.202200003,10.1002/ajoc.202100665,10.1002/anie.202114731,10.1039/d1qo01219c,10.1002/slct.202102062,10.1039/d1sc03596g,10.1021/acs.joc.1c00532,10.6023/cjoc202010027,10.1021/acs.orglett.1c00940,10.1039/d1qo00380a,10.1021/acs.orglett.1c00551,10.1016/j.tet.2021.131955,10.1002/anie.202014660,10.1021/acs.orglett.0c03342,10.1021/acs.orglett.0c03210,10.1021/acs.orglett.0c02462,10.1021/acs.accounts.0c00291,10.1021/jacs.0c07634,10.1039/d0ob00711k,10.1021/acs.orglett.0c01869,10.1002/anie.202002271,10.1021/acs.orglett.0c00554,10.1021/acs.orglett.0c00442,10.1002/ejoc.201901865,10.1021/acs.orglett.9b04497,10.1055/s-0039-1690158,10.1002/chem.201903668,10.1002/ejoc.201901037,10.1021/acs.orglett.9b02788,10.1039/c9cy00938h,10.1021/acs.orglett.9b01164,10.1021/jacs.9b02238,10.1002/anie.201900995,10.3390/catal9010053,10.1021/acscentsci.8b00628,10.1021/acs.orglett.8b03567,10.1002/asia.201801020,10.1016/bs.aihch.2017.10.001,10.1021/acs.chemrev.7b00234,10.6023/cjoc201703042,10.6023/cjoc201612031,10.6023/cjoc201702001,10.1021/acs.orglett.6b03158,10.1055/s-0035-1562442,10.1021/acs.orglett.6b01837,10.1007/s41061-016-0042-2,10.1021/acs.orglett.6b01134,10.1021/acs.joc.5b02853,10.1021/acs.orglett.5b03591,10.1039/c5nj01597a,10.1039/c5qo00224a3/10/2022
462
504FALSEanie.20180074910.1002/anie.201800749https://sci-hub.wf/10.1002/anie.201800749https://doi.org/10.1002/anie.201800749NiC-H ActivationxWilliam30-MayTRUE921#N/A2018
YCsp3-Csp2_arHXHBrAlkylArylK3PO4Ionic-PO4Nu-H6/1/2022
463
505FALSEacscatal.0c0131810.1021/acscatal.0c01318https://sci-hub.wf/10.1021/acscatal.0c01318https://doi.org/10.1021/acscatal.0c01318NiC-H ActivationxWilliam30-MayTRUE481#N/A2020
YCsp3-Csp3HXHBrAlkylAlkylK3PO4Ionic-PO4Nu-H6/1/2022
464
506FALSEacs.orglett.7b0382610.1021/acs.orglett.7b03826https://sci-hub.wf/10.1021/acs.orglett.7b03826https://doi.org/10.1021/acs.orglett.7b03826NiC-H ActivationxWilliam30-MayTRUE471#N/A2018
yCsp3-Csp3HXHXAlkylAlkylNo baseNo BaseNu-H6/1/2022
465
507FALSEjacs.9b0701410.1021/jacs.9b07014https://sci-hub.wf/10.1021/jacs.9b07014https://doi.org/10.1021/jacs.9b07014NiC-H ActivationxWilliam30-MayTRUE731#N/A2019
yCsp3-Csp3HXHBrAlkylAlkylK3PO4Ionic-PO4Nu-H6/1/2022
466
508FALSEacscatal.1c0431410.1021/acscatal.1c04314https://sci-hub.wf/10.1021/acscatal.1c04314https://doi.org/10.1021/acscatal.1c04314NiC-H ActivationxWilliam30-MayTRUE101#N/A2021
yCsp3-Csp2HXHBrAlkylVinylK2CO3Ionic-CO3Nu-H6/1/2022
467
509FALSEacscatal.0c0569410.1021/acscatal.0c05694https://sci-hub.wf/10.1021/acscatal.0c05694https://doi.org/10.1021/acscatal.0c05694NiC-H ActivationxWilliam30-MayTRUE281#N/A2021
yCsp3-Csp2_arHXHBrAlkylArylNo baseNo BaseNu-H6/1/2022
468
510FALSEjacs.6b0478910.1021/jacs.6b04789https://sci-hub.wf/10.1021/jacs.6b04789https://doi.org/10.1021/jacs.6b04789NiC-H ActivationxWilliam30-MayTRUE1081#N/A2016
yCsp3-Csp3-ring(s)HXHBrAlkyl
Csp3-(Het)(Ar)
K2HPO4Nu-H6/1/2022
469
511FALSEscience.abh262310.1126/science.abh2623https://sci-hub.wf/10.1126/science.abh2623https://doi.org/10.1126/science.abh2623NiC-H ActivationxWilliam30-MayTRUE441#N/A2021
YCsp3-Csp3HCsp3HCH3AlkylAlkylNo baseNo BaseNu-H6/1/2022
470
512FALSEs41586-018-0366-x10.1038/s41586-018-0366-xhttps://sci-hub.wf/10.1038/s41586-018-0366-xhttps://doi.org/10.1038/s41586-018-0366-xNiC-H ActivationxWilliam30-MayTRUE2311#N/A2018
YCsp3-Csp2_arHXHBrAlkylArylK3PO4Ionic-PO4Nu-H6/1/2022
471
270FALSEc5sc02942b10.1039/c5sc02942bhttps://sci-hub.wf/10.1039/c5sc02942bhttps://doi.org/10.1039/c5sc02942bNiC-O ActivationLong10-MarTRUE886802015Itami, K
Alkyl-aryl ketone synthesis via nickel-catalyzed reductive coupling of alkyl halides with aryl acids and anhydrides
CHEMICAL SCIENCE
The present work disclosed a considerably improved method for the construction of alkyl-aryl ketones by the direct coupling of unactivated alkyl bromides with 1.5 equiv. of acids. In addition, the synthesis of aroyl C-glycosides was first achieved by the reductive coupling of 1-glycosyl bromides with acid derivatives, which may otherwise require multi-step synthesis.
9/8/2015Csp2_ar-Csp2_arE-NuOH
OCONMe2
HArylHetK3PO4Ionic-PO4Medium0.31_10.1021/acscatal.6b01120,10.1021/acscatal.8b03436,10.1021/acs.orglett.6b02265,10.1021/acscatal.0c00291,10.1021/jacs.7b04973,10.1002/anie.20151074310.1002/aoc.6551,10.1016/j.ica.2021.120747,10.1016/j.chempr.2021.08.001,10.1002/adsc.202100992,10.1021/acs.orglett.1c02346,10.1016/j.poly.2021.115412,10.3762/bjoc.17.126,10.1021/jacs.1c04215,10.1002/chem.202100475,10.1002/tcr.202100113,10.1021/acs.orglett.1c00100,10.1016/j.ica.2020.120043,10.1021/acs.joc.0c02151,10.1055/a-1349-3543,10.3390/molecules25214970,10.1021/acs.chemrev.0c00088,10.1021/acsmaterialslett.0c00206,10.1021/acs.chemrev.9b00682,10.1002/aoc.5869,10.1055/s-0040-1708003,10.1016/j.chempr.2020.04.005,10.1002/cjoc.201900506,10.1016/j.molstruc.2019.127668,10.1021/acsomega.9b04450,10.1021/acscatal.0c00291,10.1002/jccs.201900450,10.1021/acs.joc.9b02094,10.1016/j.jcat.2019.07.026,10.1021/acs.organomet.9b00340,10.1002/anie.201904774,10.1021/acs.organomet.9b00060,10.1002/adsc.201801381,10.1039/c9cy00009g,10.1039/c9ob00144a,10.1021/acs.chemrev.8b00507,10.1007/3418_2018_19,10.3390/catal9010076,10.1021/acscatal.8b03436,10.1021/acscatal.8b03770,10.1016/j.tet.2018.10.025,10.1055/s-0037-1611012,10.1002/asia.201800478,10.1039/c8ob01034j,10.1016/j.jorganchem.2018.01.019,10.1002/adsc.201701506,10.1002/adsc.201701515,10.1021/acs.orglett.8b00080,10.1039/c7cc08709h,10.1039/c7dt04560c,10.1039/c7ta08389k,10.1021/acs.joc.7b02612,10.1055/s-0036-1589120,10.1039/c7cs00182g,10.1021/acscatal.7b02540,10.1021/jacs.7b04973,10.1021/acs.orglett.7b01938,10.1039/c7qo00174f,10.1039/c7qo00068e,10.1055/s-0036-1588734,10.1002/cssc.201700321,10.1002/slct.201700623,10.1016/j.tet.2017.02.021,10.1246/bcsj.20160365,10.1021/jacs.7b00049,10.1021/acscatal.6b02988,10.1002/anie.201610409,10.1039/c6sc04371b,10.1021/acscatal.6b02964,10.1002/slct.201601747,10.1007/s40010-016-0289-6,10.1021/acs.orglett.6b02619,10.1002/anie.201606529,10.1021/acs.orglett.6b02265,10.1002/chem.201603092,10.1039/c6cc03956a,10.1007/s41061-016-0043-1,10.1007/s41061-016-0053-z,10.1021/acscatal.6b01120,10.1246/cl.160133,10.1002/anie.201510743,10.1016/bs.adomc.2016.07.001,10.1039/c6ra14670h11/4/2021
472
514FALSEjacs.6b0953310.1021/jacs.6b09533https://sci-hub.wf/10.1021/jacs.6b09533https://doi.org/10.1021/jacs.6b09533NiCheating ?xWilliam30-MayFALSE3161#N/A2016
MacMillan, DWC
#N/A
Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: sp(3)-sp(2) Cross-Coupling of Oxalates with Aryl Halides
9/10/2016y#N/A
473
515FALSEd0sc01445a10.1039/d0sc01445ahttps://sci-hub.wf/10.1039/d0sc01445ahttps://doi.org/10.1039/d0sc01445aNiC-H ActivationxWilliam31-MayTRUE391#N/A2020
yCsp2_ar-Csp3-ring(s)HXHBrAryl
Csp3-(Het)(Ar)
Lutidine Nu-H6/9/2022
474
516FALSEanie.20210898710.1002/anie.202108987https://sci-hub.wf/10.1002/anie.202108987https://doi.org/10.1002/anie.202108987NiC-H ActivationxWilliam31-MayTRUE111#N/A2021
Csp3-Csp2HXHClAlkyl
Carbonyl
Lutidine Nu-H6/9/2022
475
517FALSEd1cc06247f10.1039/d1cc06247fhttps://sci-hub.wf/10.1039/d1cc06247fhttps://doi.org/10.1039/d1cc06247fNiC-H ActivationxWilliam1-JunTRUE01#N/A2022
Csp3-Csp3HXHFAlkylAlkylNo baseNo BaseNu-H6/9/2022
476
43FALSEc7cc01932g10.1039/c7cc01932ghttps://sci-hub.wf/10.1039/c7cc01932ghttps://doi.org/10.1039/c7cc01932gNiC-O ActivationKellyTRUE36442017
Komeyama, K
C-H arylation and alkenylation of imidazoles by nickel catalysis: solvent-accelerated imidazole C-H activation
CHEMICAL COMMUNICATIONS
The first nickel-catalyzed C-H arylations and alkenylations of imidazoles with phenol and enol derivatives are described. Under the influence of Ni(OTf)(2)/dcype/K3PO4 (dcype: 1,2-bis(dicyclohexylphosphino) ethane) in t-amyl alcohol, imidazoles can undergo C-H arylation with phenol derivatives. The C-H arylation of imidazoles with chloroarenes as well as that of thiazoles and oxazoles with phenol derivatives can also be achieved with this catalytic system. By changing the ligand to dcypt (3,4-bis(dicyclohexylphosphino) thiophene), enol derivatives could also be employed as coupling partners achieving the C-H alkenylation of imidazoles as well as thiazoles and oxazoles. Thus, a range of C2-arylated and alkenylated azoles can be synthesized using this newly developed nickel-based catalytic system. The key to the success of the C-H coupling of imidazoles is the use of a tertiary alcohol as solvent. This also allows the use of an air-stable nickel(II) salt as the catalyst precursor.
Hiroshima Univ6/18/2017yCsp3-Csp2_arE-EOXOTsIAlkylAryl#N/ANo BaseWeak0.36_xxx10.1021/jacs.0c13093,10.1021/jacs.0c01330,10.1039/c9sc03347e,10.1021/acscatal.9b0335210.1039/d1ra07252h,10.1055/s-0041-1737762,10.1021/jacs.1c11170,10.1021/acs.orglett.1c02893,10.1055/s-0040-1707817,10.1142/S1088424621500528,10.1021/jacs.1c00659,10.1021/jacs.0c13093,10.1039/d0ra10739e,10.1055/s-0040-1706602,10.1021/acscatal.0c03237,10.1021/acsomega.0c04181,10.1002/ijch.202000069,10.1002/ejoc.202000270,10.1021/jacs.0c01330,10.1021/jacs.0c00245,10.1039/c9cc09377j,10.1002/ajoc.201900625,10.1039/c9sc03347e,10.1021/acscatal.9b03352,10.1021/acs.chemrev.8b00715,10.3390/molecules24081458,10.1002/anie.201812702,10.6023/cjoc201806038,10.1021/jacs.8b12634,10.1021/jacs.8b06458,10.1021/acs.orglett.8b01863,10.1021/acs.orglett.8b00235,10.1021/acs.orglett.7b036992/7/2022
477
519FALSEjacs.1c0815710.1021/jacs.1c08157https://sci-hub.wf/10.1021/jacs.1c08157https://doi.org/10.1021/jacs.1c08157NiC-H ActivationxJustin1-JunTRUE71#N/A2021
Csp2_ar-Csp2_arHXHBrArylArylNa2CO3Ionic-CO3Nu-H6/21/2022
478
520FALSEjacs.2c0232910.1021/jacs.2c02329https://sci-hub.wf/10.1021/jacs.2c02329https://doi.org/10.1021/jacs.2c02329NiC-H ActivationxJustin2-JunFALSE61#N/A2022#N/A#N/A
479
521FALSEjacs.8b0919110.1021/jacs.8b09191https://sci-hub.wf/10.1021/jacs.8b09191https://doi.org/10.1021/jacs.8b09191NiC-H ActivationxChun Hey2-JunFALSE531#N/A2018#N/Ay#N/A
480
522FALSEacs.orglett.9b0109710.1021/acs.orglett.9b01097https://sci-hub.wf/10.1021/acs.orglett.9b01097https://doi.org/10.1021/acs.orglett.9b01097NiC-N ActivationxJustin3-JunTRUE891#N/A2019
Csp2_ar-Csp3XNBr
Triphenylpyridinium+BF4-
ArylAlkylNo baseNo Base6/21/2022
481
88FALSEc7cc06106d10.1039/c7cc06106dhttps://sci-hub.wf/10.1039/c7cc06106dhttps://doi.org/10.1039/c7cc06106dNiC-O ActivationGerryTRUE52512017Gong, HG
Highly nucleophilic vitamin B-12-assisted nickel-catalysed reductive coupling of aryl halides and non-activated alkyl tosylates
CHEMICAL COMMUNICATIONS
Reductive cross-coupling of aryl halides with ubiquitous alkyl tosylates was developed using a combination of nickel and vitamin B-12 (VB12: cyanocobalamin) catalysts. The tosylate was activated by reduced VB12 to form alkyl cobalt(III), which served as a good alkylating agent for aryl-nickel species, leading to C(sp(3))- C(sp(2)) bond formation.
Shanghai Univ9/18/2017Csp3-Csp2_arE-EOXOTsBrAlkylArylNitrogenNitrogen(charged)Weak0.36_10.1021/acs.orglett.9b00174,10.1021/jacs.0c13093,10.1021/jacs.0c12462,10.1039/c9sc03347e,10.1021/jacs.0c0133010.1039/d2ra00010e,10.1055/s-0041-1737762,10.1021/jacs.1c11170,10.1021/acs.joc.1c02188,10.6023/cjoc202106021,10.1039/d1ob01874d,10.1021/acs.orglett.1c02458,10.1002/anie.202106273,10.1021/acs.joc.1c01325,10.1039/c9cs00571d,10.1039/d1qo00549a,10.1039/d1qo00358e,10.1021/jacs.0c13057,10.1021/acs.orglett.1c00280,10.1021/jacs.0c13093,10.1021/acs.accounts.0c00694,10.1021/jacs.0c12462,10.6023/cjoc202006075,10.1021/acs.joc.0c01909,10.1021/acsomega.0c04181,10.1002/adsc.202000985,10.1039/d0sc03217d,10.1021/acs.accounts.0c00291,10.1021/acs.joc.0c01274,10.1002/chem.202001180,10.1039/d0gc01183e,10.1021/jacs.0c02805,10.1021/jacs.0c01330,10.1039/c9cc09377j,10.1021/acs.joc.9b02431,10.1002/slct.201903251,10.1002/asia.201901490,10.1021/jacs.9b07857,10.1039/c9sc03347e,10.1016/j.tetlet.2019.150991,10.1039/c9ob01173k,10.1021/acs.orglett.9b00174,10.1002/chem.201803642,10.6023/cjoc201806038,10.1021/acs.orglett.9b00100,10.1021/acs.joc.8b02701,10.1021/acs.orglett.8b02498,10.1021/acs.orglett.8b01863,10.1002/anie.201803228,10.1021/acs.orglett.8b002351/20/2022
482
524FALSEd0cc01480j10.1039/d0cc01480jhttps://sci-hub.wf/10.1039/d0cc01480jhttps://doi.org/10.1039/d0cc01480jNiC-H ActivationxChun Hey3-JunTRUE151#N/A2020
yCsp3-ring(s)-Csp2HXHClBenzyl
Carbonyl
K2HPO4Nu-H6/1/2022
483
21FALSEc7cc06717h10.1039/c7cc06717hhttps://sci-hub.wf/10.1039/c7cc06717hhttps://doi.org/10.1039/c7cc06717hNiC-O ActivationTRUE94592017Iranpoor, N
Nickel-catalyzed methylation of aryl halides/tosylates with methyl tosylate
CHEMICAL COMMUNICATIONS
This work describes the cross-electrophile methylation of aryl bromides and aryl tosylates with methyl tosylate. The mild reaction conditions allow effective methylation of a wide set of heteroaryl electrophiles and dimethylation of dibromoarenes.
Shiraz Univ12/11/2017Csp2_ar-Csp2E-NuOH
2-methyl-4,6-bis(p-tolyloxy)-1,3,5-triazine
HArylVinylIonic-PO4Strong-0.32_x10.1039/c9sc03347e,10.1021/acs.orglett.9b00174,10.1021/jacs.0c13093,10.1021/jacs.0c1246210.1039/d1nj01762d,10.1002/cctc.202000876,10.1021/acs.chemrev.9b00682,10.1039/c9cc08727c,10.1002/slct.201804066,10.1021/acsomega.9b00567,10.1016/j.cclet.2018.09.009,10.1039/c8ob01034j,10.1021/acs.orglett.8b009742/17/2022
484
526FALSEanie.20180511810.1002/anie.201805118https://sci-hub.wf/10.1002/anie.201805118https://doi.org/10.1002/anie.201805118NiC-H ActivationxJustin9-JunTRUE681#N/A2018
Csp2_ar-Csp3XHBrHArylAlkyl2,6-Lutidine6/21/2022
485
527FALSEanie.20220166210.1002/anie.202201662https://sci-hub.wf/10.1002/anie.202201662https://doi.org/10.1002/anie.202201662NiC-H ActivationxJustin10-JunTRUE01#N/A2022
#N/AXHBrHAlkylNR2pyridineNitrogenNitrogen(neutral)6/21/2022
486
528https://sci-hub.wf/https://doi.org/NiWilliam10-Jun3361#N/A#N/A#N/A
487
532FALSEjacs.8b1202510.1021/jacs.8b12025https://sci-hub.wf/10.1021/jacs.8b12025https://doi.org/10.1021/jacs.8b12025NiCheating ?xWilliam11-JunTRUE961#N/A2018
MacMillan, DWC
Metallaphotoredox-Catalyzed Cross-Electrophile C-sp(3)-C-sp(3) Coupling of Aliphatic Bromides
12/19/2022Csp3-Csp3E-EOXOTsBrAlkylAlkylNa2CO3Ionic-CO3Weak0.366/15/2022
488
533FALSEc9cc04726c10.1039/c9cc04726chttps://sci-hub.wf/10.1039/c9cc04726chttps://doi.org/10.1039/c9cc04726cNiC-H ActivationxJustin11-JunTRUE281#N/A2019
Csp2_ar-Csp2XHBrHAryl
Carbonyl
Na2CO3Ionic-CO36/21/2022
489
536FALSEjacs.9b1255410.1021/jacs.9b12554https://sci-hub.wf/10.1021/jacs.9b12554https://doi.org/10.1021/jacs.9b12554NiC-H activationxJustin11-JunFALSE421#N/A#N/A#N/A
490
137FALSEc7sc03140h10.1039/c7sc03140hhttps://sci-hub.wf/10.1039/c7sc03140hhttps://doi.org/10.1039/c7sc03140hNiC-O ActivationShihongTRUE801002018Shu, XZ
Efficient Ni-catalyzed conversion of phenols protected with 2,4,6-trichloro-1,3,5-triazine (TCT) to olefins
CHEMICAL SCIENCE
An efficient Ni(COD)(2)/dppf catalyzed olefination of Ar-O-TCT as synthetic equivalents of aryl halides is described. Activation of C-O bonds in phenols as readily available compounds was achieved with 2,4,6-trichloro-1,3,5-triazine (TCT). This method provides practical access to 1,2-disubstituted olefins in high yields and high functional group compatibility.
Lanzhou Univ1/21/2018Csp3-Csp2_arE-EOXOHBrAllylArylNo baseNo BaseStrong-0.81_10.1021/jacs.0c12462,10.1002/anie.201805611,10.1021/acscatal.0c01356,10.1039/c9sc03347e,10.1021/jacs.0c13093,10.1021/jacs.9b03863,10.1021/jacs.9b05224,10.1039/c8sc00609a,10.1021/acs.orglett.9b01164,10.1002/anie.20211455610.1002/anie.202200215,10.1021/acs.orglett.2c00207,10.1038/s42004-022-00633-3,10.1021/acscatal.1c05530,10.1021/acs.orglett.1c03776,10.1002/anie.202114556,10.1002/chem.202103643,10.1002/ejic.202100820,10.1021/acscatal.1c04128,10.1021/acscatal.1c04239,10.1002/anie.202112876,10.6023/cjoc202106021,10.1039/d1qo01474a,10.1039/d1ob01874d,10.1021/acs.orglett.1c02893,10.1016/j.chempr.2021.09.006,10.1021/jacs.1c08695,10.1021/acs.orglett.1c02938,10.1038/s41586-021-03920-6,10.1021/acs.orglett.1c02616,10.1021/jacs.1c05670,10.1021/jacs.1c06271,10.1039/d1nj02677a,10.1002/anie.202107492,10.1039/c9cs00571d,10.1039/d1sc02547c,10.1002/adsc.202100116,10.1055/a-1467-2432,10.1021/jacs.1c00618,10.1021/acs.orglett.1c00280,10.1055/a-1406-0484,10.1021/jacs.0c13093,10.1021/jacs.0c12462,10.1002/bkcs.12211,10.1055/s-0040-1707342,10.1002/anie.202010737,10.1039/d0cc05895e,10.1021/jacs.0c07492,10.1021/acs.chemrev.9b00682,10.1002/anie.202006322,10.1002/adsc.202000186,10.1039/d0sc01471k,10.1021/acscatal.0c01356,10.1002/anie.201915454,10.1055/s-0039-1691525,10.1016/j.tetlet.2020.151758,10.1016/j.tetlet.2020.151729,10.3390/nano10040632,10.1021/acs.orglett.0c00561,10.1039/c9cc07072a,10.1021/acs.orglett.9b03633,10.1021/jacs.9b10026,10.1039/c9sc03347e,10.1016/j.tetlet.2019.150991,10.1021/jacs.9b05224,10.3390/molecules24122296,10.1021/acs.orglett.9b01164,10.1021/jacs.9b03863,10.6023/cjoc201812051,10.6023/cjoc201806038,10.6023/cjoc201810020,10.1021/jacs.8b08190,10.1021/acs.joc.8b01474,10.1002/anie.201805611,10.1039/c8sc00609a,10.1021/acs.organomet.7b00894,10.1021/acs.orglett.8b00114,10.2533/chimia.2018.212 Long 1/5/2022
491
276FALSEc7sc05216b10.1039/c7sc05216bhttps://sci-hub.wf/10.1039/c7sc05216bhttps://doi.org/10.1039/c7sc05216bNiC-O ActivationGerry14-MarTRUE341712018Stoltz, BM
Dual nickel and Lewis acid catalysis for cross-electrophile coupling: the allylation of aryl halides with allylic alcohols
CHEMICAL SCIENCE
Controlling the selectivity in cross-electrophile coupling reactions is a significant challenge, particularly when one electrophile is much more reactive. We report a general and practical strategy to address this problem in the reaction between reactive and unreactive electrophiles by a combination of nickel and Lewis acid catalysis. This strategy is used for the coupling of aryl halides with allylic alcohols to form linear allylarenes selectively. The reaction tolerates a wide range of functional groups (e.g. silanes, boronates, anilines, esters, alcohols, and various heterocycles) and works with various allylic alcohols. Complementary to most current routes for the C3 allylation of an unprotected indole, this method provides access to C2 and C4-C7 allylated indoles. Preliminary mechanistic experiments reveal that the reaction might start with an aryl nickel intermediate, which then reacts with Lewis acid activated allylic alcohols in the presence of Mn.
3/7/2018Csp3-Csp3E-NuOHOHHAllylAlkylNo baseNo BaseStrong-0.81_10.1021/acscatal.0c0135610.1039/d1qo01927a,10.1002/ejic.202100820,10.1021/acscatal.1c03729,10.1021/acscatal.1c03449,10.1021/acscatal.1c02790,10.1021/acs.chemrev.0c00564,10.1002/asia.202100432,10.3390/catal11050526,10.1039/d1qo00490e,10.1016/j.tetlet.2021.152916,10.1039/d0ob02489a,10.1021/acs.chemrev.0c01115,10.1055/a-1389-1203,10.1039/d0sc04383d,10.1039/d0cc02058c,10.1021/acscatal.0c01356,10.1039/c9gc04306c,10.1021/acs.orglett.0c01109,10.1002/anie.202000704,10.1002/anie.201913518,10.1002/anie.201912618,10.1021/acs.orglett.9b03633,10.1021/acs.joc.9b01293,10.1002/ajoc.201900299,10.1039/c9sc00633h,10.1002/adsc.201801606,10.1021/jacs.9b00788,10.1021/acs.orglett.8b04030,10.6023/cjoc201809037,10.1021/jacs.8b08746,10.1039/c8qo00827b,10.1002/cjoc.2018002373/15/2022
492
256FALSEc8qo00764k10.1039/c8qo00764khttps://sci-hub.wf/10.1039/c8qo00764khttps://doi.org/10.1039/c8qo00764kNiC-O ActivationGerry24-FebTRUE321332018Balaraman, E
Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
ORGANIC CHEMISTRY FRONTIERS
The first nickel-catalyzed enantioselective allylic alkylation of lactone and lactam substrates to deliver products bearing an all-carbon quaternary stereocenter is reported. The reaction, which utilizes a commercially available chiral bisphosphine ligand, proceeds in good yield with a high level of enantioselectivity (up to 90% ee) on a range of unactivated allylic alcohols for both lactone and lactam nucleophiles. The utility of this method is further highlighted via a number of synthetically useful product transformations.
11/21/2018Csp3-Csp3-ring(s)E-NuOHOHHAlkylBenzylIonic-OtBuStrong-0.81_10.1002/cctc.202101455,10.1039/d1cc05899a,10.1002/adsc.202101077,10.1002/tcr.202100165,10.1021/acs.organomet.1c00328,10.1039/d1ob01154e,10.1039/d1qo00930c,10.1002/ejoc.202100420,10.1039/d1nj01581h,10.1039/d1ob00080b,10.1002/ajoc.202000634,10.1002/ajoc.202000631,10.1002/ejoc.202001109,10.1016/j.jcat.2020.07.032,10.1021/acs.orglett.0c02635,10.1002/ejoc.202000781,10.1021/acs.orglett.0c01851,10.1021/acs.joc.0c00561,10.1016/j.tetlet.2020.151885,10.1039/d0cc01593h,10.1021/acs.joc.9b02913,10.1021/acs.joc.9b03104,10.1039/c9ob01559k,10.1039/c9cc08448g,10.1002/ejoc.201901331,10.1246/cl.190488,10.1021/acs.joc.9b01517,10.1002/adsc.201900447,10.1039/c9cc03591e2/28/2022
493
542FALSEacs.orglett.7b0155210.1021/acs.orglett.7b01552https://sci-hub.wf/10.1021/acs.orglett.7b01552https://doi.org/10.1021/acs.orglett.7b01552NiC-H ActivationxJustin12-JunTRUE431#N/A
#N/AHXHClNR2
Carbonyl
K3PO4Ionic-PO4Nu-H6/21/2022
494
83FALSEc8sc00609a10.1039/c8sc00609ahttps://sci-hub.wf/10.1039/c8sc00609ahttps://doi.org/10.1039/c8sc00609aNiC-O ActivationGerryTRUE591102018Shu, XZ
Ni-Catalyzed dehydrogenative coupling of primary and secondary alcohols with methyl-N-heteroaromatics
CHEMICAL SCIENCE
Here we report the first base-metal catalyzed dehydrogenative coupling of primary (aromatic, heteroaromatic, and aliphatic) and secondary alcohols with methyl-N-heteroaromatics to form various C(sp(3))-alkylated N-heteroaromatics. The reaction is enabled by Earth abundant, non-precious NiBr2 as a transition metal catalyst and N,N,N,N-tetramethylethylenediamine (TMEDA) as a ligand system. Mechanistic studies reveal that a hydrogen auto-transfer process is involved in the direct C(sp(3))-alkylation and the reaction proceeds through an -olefination process.
Lanzhou Univ5/21/2018Csp3-ring(s)-Csp3E-EOX
Monomethyl Oxalate
BrBenzylAlkylNo baseNo BaseStrong0.13_xxx10.1039/c9sc03347e,10.1039/c9sc00783k,10.1021/acscatal.1c05208,10.1021/acscatal.9b03352,10.1021/acs.orglett.9b00174,10.1021/jacs.8b12801,10.1021/jacs.0c13093,10.1021/acs.orglett.9b01164,10.1021/acscatal.1c05208,10.1021/jacs.9b05224,10.1021/jacs.0c1246210.1021/acs.orglett.2c00207,10.1055/s-0040-1719881,10.1055/s-0041-1737762,10.1021/acs.joc.1c02897,10.1021/acscatal.1c05530,10.1021/acscatal.1c05208,10.1039/d1qo01614h,10.1021/acscatal.1c04239,10.6023/cjoc202106021,10.1021/acs.orglett.1c02874,10.1021/jacs.1c08695,10.1039/d1sc04011a,10.1016/j.tetlet.2021.153129,10.1246/cl.210015,10.1055/a-1467-2432,10.1055/a-1406-0484,10.1021/jacs.0c13093,10.1021/acs.orglett.0c02934,10.1021/jacs.0c12462,10.1055/s-0040-1707342,10.1038/s41467-020-19194-x,10.1021/jacs.0c07492,10.1016/j.chempr.2020.04.006,10.1002/aoc.5741,10.1055/s-0039-1691525,10.1021/acs.orglett.0c00688,10.1021/acs.orglett.0c00561,10.1039/c9cc07072a,10.1021/acs.joc.9b02431,10.1039/c9sc03347e,10.1021/acscatal.9b03352,10.1016/j.tetlet.2019.150991,10.1021/jacs.9b05224,10.1021/acs.orglett.9b01987,10.1021/acs.joc.9b00649,10.1021/acs.orglett.9b01164,10.1039/c9ob00628a,10.1039/c9sc00783k,10.1021/acs.orglett.9b00692,10.1021/acs.orglett.9b00174,10.1039/c8sc04335c,10.1021/jacs.8b12801,10.1039/c8qo01044g,10.1021/acscatal.8b03930,10.1002/slct.201802644,10.1002/adsc.201800879,10.1021/acscatal.8b027841/5/2022
495
544FALSEjacs.0c0172410.1021/jacs.0c01724https://sci-hub.wf/10.1021/jacs.0c01724https://doi.org/10.1021/jacs.0c01724NiC-N ActivationxJustin12-JunTRUE191#N/A
Csp3-Csp2_arNX
N(Ring-Opening)
IAlkylArylEt3NNitrogenNitrogen(neutral)6/21/2022
496
545https://sci-hub.wf/https://doi.org/Ni12-Jun361#N/A2020Xue, D#N/A
Light-Promoted Nickel Catalysis: Etherification of Aryl Electrophiles with Alcohols Catalyzed by a Ni-II-Aryl Complex
7/27/2022#N/A
497
546FALSEanie.20200444110.1002/anie.202004441https://sci-hub.wf/10.1002/anie.202004441https://doi.org/10.1002/anie.202004441NiC-N ActivationxJustin12-JunTRUE361#N/A
Csp2-Csp3NH
pyrrolidine-2,5-dione
H
Carbonyl
AlkylK2CO3Ionic-CO36/21/2022
498
547FALSEacs.orglett.7b0374710.1021/acs.orglett.7b03747https://sci-hub.wf/10.1021/acs.orglett.7b03747https://doi.org/10.1021/acs.orglett.7b03747NiC-N ActivationxJustin12-JunTRUE291#N/A
Csp3-Csp2_arNB
N(Ring-Opening)
BF3KAlkylArylNo baseNo Base6/21/2022
499
253FALSEc9cc08079a10.1039/c9cc08079ahttps://sci-hub.wf/10.1039/c9cc08079ahttps://doi.org/10.1039/c9cc08079aNiC-O ActivationGerry21-FebTRUE141#N/A2020Hu, R
Allylation of aldehydes by dual photoredox and nickel catalysis
CHEMICAL COMMUNICATIONS
Here we report the application of dual nickel/photoredox catalysis to the allylation of aliphatic, aromatic and heteroaromatic aldehydes by using commercially available reagents. The process utilizes the combination of a Ni(II) complex, [Ru(bpy)(3)](2+) as a photoredox catalyst, and allylacetate under blue LED irradiation, and allows the synthesis of a large variety of homoallylic alcohols.
1/4/2020Csp3-Csp2_arE-NuOB
O(Ring-Opening)
B(OH)2AlkylArylNo baseNo BaseWeak1_10.1039/d2ob00065b,10.1039/d2cc00461e,10.1016/j.chempr.2021.10.023,10.1016/j.tetlet.2021.153369,10.1007/s13738-021-02373-y,10.1021/acscatal.1c00536,10.1002/adsc.202001493,10.1039/d0qo01016b,10.1021/acs.orglett.0c02478,10.1039/d0ra02195d,10.1039/d0ob00535e,10.1021/acscatal.0c011992/28/2022
500
36FALSEc9sc03347e10.1039/c9sc03347ehttps://sci-hub.wf/10.1039/c9sc03347ehttps://doi.org/10.1039/c9sc03347eNiC-O ActivationKellyTRUE30302019Shu, XZ
Base-free Ni-catalyzed Suzuki-type cross-coupling reactions of epoxides with boronic acids
CHEMICAL SCIENCE
A Ni-catalyzed Suzuki-type cross-coupling of boronic acids with epoxides without an exogenous base and with broad substrate scope has been developed. The product selectivity of styrenyl epoxides is different from that of previous work. This methodology uses readily available starting materials to access a range of substituted alcohols, which are valuable feedstock chemicals.
Lanzhou Univ10/7/2019xCsp2-Csp2_arE-EOOOTfOMsVinylArylNo baseNo BaseWeak0.53_xx10.1002/anie.202114556,10.1021/jacs.0c01330,10.1021/jacs.0c1246210.1002/anie.202200215,10.1021/jacs.1c11170,10.1002/anie.202114556,10.1002/anie.202112876,10.1021/acs.orglett.1c02893,10.1021/acs.orglett.1c02874,10.1021/jacs.1c08695,10.1002/anie.202106273,10.1021/acs.orglett.1c01879,10.1016/j.rser.2021.111103,10.1021/jacs.1c00142,10.1055/a-1406-0484,10.1021/jacs.0c12462,10.1055/s-0040-1707342,10.1002/anie.202010737,10.1021/acscatal.0c03237,10.1021/acsomega.0c04181,10.1021/jacs.0c07492,10.1002/ejoc.202000623,10.1021/jacs.0c04812,10.1021/acs.orglett.0c01683,10.1016/j.tet.2020.131103,10.1055/s-0039-1691525,10.1021/jacs.0c01330,10.1039/c9cc09377j Long 1/16/2022
501
550FALSEacscatal.1c0141610.1021/acscatal.1c01416https://sci-hub.wf/10.1021/acscatal.1c01416https://doi.org/10.1021/acscatal.1c01416NiC-N ActivationxJustin12-JunTRUE141#N/A
Csp3-Csp2_arNX
Triphenylpyridinium+BF4-
BrAlkylArylNo baseNo Base6/21/2022
502
18FALSEd0sc05452f10.1039/d0sc05452fhttps://sci-hub.wf/10.1039/d0sc05452fhttps://doi.org/10.1039/d0sc05452fNiC-O ActivationGerryTRUE9112021Gong, HG
Ni-catalyzed cross-electrophile coupling between vinyl/aryl and alkyl sulfonates: synthesis of cycloalkenes and modification of peptides
CHEMICAL SCIENCE
We report here the coupling reactions between vinyl/aryl and alkyl C-O electrophiles that can be derived from chemical feedstocks and naturally occurring functional groups. This method provides an efficient approach to the synthesis of a wide range of functionalized, and/or secondary alkyl substituted cycloalkenes. These compounds are difficult to produce by conventional methods. The reaction proceeds with broad substrate scope, and tolerates various functional groups such as alcohol, aldehyde, ketone, ester, amide, alkene, alkyne, heterocycles, organotin and organosilicon compounds. The synthetic utility of this method has been demonstrated by providing facile access to important building blocks. We also demonstrated the possibility to apply this method for late-stage modification of peptides. A broad range of functionalized alkyl groups could be selectively introduced into tyrosine in peptides via C-C bond formation, which has been a challenge to the existing procedures.
Shanghai Univ1/7/2021Csp3-Csp2E-EOXOPivBrAlkylVinylNitrogenNitrogen(charged)Medium0.33_10.6023/cjoc202106021,10.1039/d1gc03230e,10.1039/d1qo01284c,10.1021/acs.orglett.1c02887,10.1021/acs.orglett.1c02601,10.1039/d1sc00283j,10.1039/d0sc06666d1/20/2022
503
552FALSEjacs.1c1015010.1021/jacs.1c10150https://sci-hub.wf/10.1021/jacs.1c10150https://doi.org/10.1021/jacs.1c10150NiC-N ActivationxJustin12-JunFALSE61#N/A#N/A#N/A
504
1FALSEd1cc00634g10.1039/d1cc00634ghttps://sci-hub.wf/10.1039/d1cc00634ghttps://doi.org/10.1039/d1cc00634gNiC-O ActivationGerryTRUE4172021Zhou, JS
Preparation of alpha-amino acids via Ni-catalyzed reductive vinylation and arylation of alpha-pivaloyloxy glycine
CHEMICAL COMMUNICATIONS
This work emphasizes easy access to alpha-vinyl and aryl amino acids via Ni-catalyzed cross-electrophile coupling of bench-stable N-carbonyl-protected alpha-pivaloyloxy glycine with vinyl/aryl halides and triflates. The protocol permits the synthesis of alpha-amino acids bearing hindered branched vinyl groups, which remains a challenge using the current methods. On the basis of experimental and DFT studies, simultaneous addition of glycine alpha-carbon (Gly) radicals to Ni(0) and Ar-Ni(ii) may occur, with the former being more favored where oxidative addition of a C(sp(2)) electrophile to the resultant Gly-Ni(i) intermediate gives a key Gly-Ni(iii)-Ar intermediate. The auxiliary chelation of the N-carbonyl oxygen to the Ni center appears to be crucial to stabilize the Gly-Ni(i) intermediate.
Peking Univ4/25/2021Csp2_ar-Csp2E-NuOHOTfHArylVinylNo baseNo BaseWeak0.53_x10.1021/jacs.1c0839910.1002/ejoc.202101384,10.1039/d1qo01579f2/22/2022
505
2FALSEd1cc02837e10.1039/d1cc02837ehttps://sci-hub.wf/10.1039/d1cc02837ehttps://doi.org/10.1039/d1cc02837eNiC-O ActivationGerryTRUE71352021Wang, XS
Nickel-catalyzed Heck reaction of cycloalkenes using aryl sulfonates and pivalates
CHEMICAL COMMUNICATIONS
Nickel-catalyzed Heck reaction of cycloalkenes delivers unusual conjugated arylated isomers. Nickel(0) catalysts ligated by chelating dialkylphosphines effectively activate not only aryl triflates as electrophiles, but also less reactive aryl mesylates, tosylates and pivalates. The omission of bases allows nickel hydride species to exist long enough to perform in situ olefin isomerization of initial Heck adducts.
Univ Sci & Technol China
9/16/2021Csp3-Csp3E-EOXOTsBrAlkylAlkylIonic-CO3Weak0.36_10.1021/jacs.1c0839910.1002/anie.202116725,10.1002/anie.2021122512/22/2022
506
555FALSEc9cc07840a10.1039/c9cc07840ahttps://sci-hub.wf/10.1039/c9cc07840ahttps://doi.org/10.1039/c9cc07840aNiC-H activationxJustin13-JunTRUE471#N/A2019
Csp2_ar-Csp3HCH
1,3-dioxoisoindolin-2-yl acetate
ArylAlkylNo baseNo BaseNu-H6/29/2022
507
556FALSEjacs.9b0417510.1021/jacs.9b04175https://sci-hub.wf/10.1021/jacs.9b04175https://doi.org/10.1021/jacs.9b04175NiC-H activationJustin13-JunTRUE1011#N/A2019
Csp3-Csp2HXHBrAlkyl
Carbonyl
NaOMeIonic-ORNu-H6/29/2022
508
557FALSEacs.orglett.9b0264310.1021/acs.orglett.9b02643https://sci-hub.wf/10.1021/acs.orglett.9b02643https://doi.org/10.1021/acs.orglett.9b02643NiC-N ActivationWilliam13-JunTRUE321#N/A2019
Csp3-Csp2_arNB
Triphenylpyridinium+BF4-
B(OH)2AlkylArylK2CO3Ionic-CO36/29/2022
509
558FALSEc5gc01931a10.1039/c5gc01931ahttps://sci-hub.wf/10.1039/c5gc01931ahttps://doi.org/10.1039/c5gc01931aNiC-H activationxWilliam14-JunTRUE771#N/A2016
Csp3-Csp2HCsp2HCOOHAlkyl
Carbonyl
Cs2CO3Ionic-CO3Nu-H6/29/2022
510
559FALSEjacs.9b1392010.1021/jacs.9b13920https://sci-hub.wf/10.1021/jacs.9b13920https://doi.org/10.1021/jacs.9b13920NiC-H activationxWilliam14-JunTRUE771#N/A2020
Csp3-Csp2HHHHAlkyl
Carbonyl
No baseNo BaseNu-H6/29/2022
511
560FALSEanie.20190180110.1002/anie.201901801https://sci-hub.wf/10.1002/anie.201901801https://doi.org/10.1002/anie.201901801NiC-H activationxWilliam16-JunTRUE441#N/A2019
Csp2-Csp3HHHH
Carbonyl
AlkylNo baseNo BaseNu-H6/29/2022
512
318FALSEa-1467-2494
10.1055/a-1467-2494
https://sci-hub.wf/10.1055/a-1467-2494https://doi.org/10.1055/a-1467-2494NiC-O Activation28-JulTRUE01#N/A2021
SYNTHESISCsp2_ar-Csp3E-NuOMgOMeMgXAryl
Csp3-Si
No baseNo BaseStrong-0.28
513
19FALSEs-0036-159086310.1055/s-0036-1590863https://sci-hub.wf/10.1055/s-0036-1590863https://doi.org/10.1055/s-0036-1590863NiC-O ActivationGerryTRUE7142017Uchiyama, M
Nickel-catalyzed reductive monofluoroakylation of alkyl tosylate with bromofluoromethane to primary alkyl fluorideSYNLETT
A nickel-catalysed direct terminal monofluoromethlyation between alkyl tosylates and a low-cost, industrial raw material bromofluoromethane has been developed. This transformation has demonstrated high efficiency, mild conditions, and good functional-group compatibility. The key to success of this transformation lies in the ligand and mild base selection, ensuring the generation of various terminal monofluormethylation products.
Univ Tokyo12/1/2017xCsp2_ar-Csp2_arE-NuOAl
OCONEt2
Al(iBu)2
ArylArylNo baseNo BaseMedium0.31_x10.1021/jacs.9b0009710.1039/d1ob00955a,10.1248/cpb.c20-00196,10.1021/acscatal.9b02636,10.1002/chem.201901163,10.1021/jacs.9b00097,10.1016/j.tet.2018.10.025,10.1055/s-0036-15920312/15/2022
514
564FALSEanie.20141032210.1002/anie.201410322https://sci-hub.wf/10.1002/anie.201410322https://doi.org/10.1002/anie.201410322NiC-H activationJustin23-JunTRUE1181#N/A
Csp2-Csp3HHHH
Carbonyl
AlkylNo baseNo BaseNu-H7/6/2022
515
565FALSEjo026170710.1021/jo0261707https://sci-hub.wf/10.1021/jo0261707https://doi.org/10.1021/jo0261707NiC-H activationJustin23-JunTRUE361#N/A
Csp1-Csp2_arHH
(Z)-methyl(styryl)selane
AlkyneArylNo baseNo BaseNu-H7/6/2022
516
566FALSEs0040-4039(03)01174-210.1016/s0040-4039(03)01174-2https://sci-hub.wf/10.1016/s0040-4039(03)01174-2https://doi.org/10.1016/s0040-4039(03)01174-2NiC-H ActivationJustin23-JunTRUE1051#N/A
Csp2_ar-Csp2_arHXHIArylArylK2CO3Ionic-CO3Nu-H7/6/2022
517
567FALSEja407671610.1021/ja4076716https://sci-hub.wf/10.1021/ja4076716https://doi.org/10.1021/ja4076716NiC-N ActivationWilliam23-JunTRUE971#N/A
Csp3-Csp3NX
N(Ring-Opening)
BrAlkylAlkylNo baseNo Base7/6/2022
518
254FALSEs-2004-83281810.1055/s-2004-832818https://sci-hub.wf/10.1055/s-2004-832818https://doi.org/10.1055/s-2004-832818NiC-O ActivationLong24-FebTRUE351542004Lin, GQ
DFT Studies Provide Mechanistic Insight into Nickel-Catalyzed Cross-Coupling Involving Organoaluminum-Mediated C-O Bond CleavageSYNLETT
Density functional theory (DFT) calculations were performed to examine the reaction pathway of Ni-catalyzed cross-coupling with organoaluminum through C-O bond cleavage. The results indicate that the strong Lewis acidity of organoaluminums significantly facilitates the transmetalation step, but not the oxidative addition or reductive elimination step.
11/3/2004Csp2-Csp2_arE-EOXOMsIVinylArylNo baseNo BaseWeak0.36_10.1002/ejoc.20100014710.1021/acscatal.1c01077,10.1002/aoc.5983,10.1007/s10600-019-02705-8,10.1039/c8qo00820e,10.3390/molecules23112810,10.3390/molecules23102417,10.1016/j.tetlet.2018.05.032,10.1016/j.bioorg.2016.09.006,10.1016/j.tet.2016.02.033,10.1039/c3ra23188g,10.1021/jo301086k,10.1039/c1sc00697e,10.1039/c2cc34551j,10.1021/cr100259t,10.1039/c1cc12240a,10.1002/ejoc.201000134,10.1055/s-0030-1258116,10.1016/j.tetlet.2009.10.096,10.1039/c004233a,10.1016/j.tet.2009.06.089,10.1002/adsc.200900287,10.1016/j.tetlet.2009.02.116,10.1021/ol802239n,10.1021/ol802049t,10.3184/030823408X338729,10.1021/jo7019064,10.1021/jo071117+,10.1016/j.tetlet.2007.03.142,10.1002/ejoc.200600469,10.1016/j.ccr.2006.02.031,10.1016/j.tetlet.2006.07.085,10.1016/j.tetlet.2006.01.020,10.1021/jo052283p,10.1021/ol052640i3/11/2022
519
260FALSEscience.abj421310.1126/science.abj4213https://sci-hub.wf/10.1126/science.abj4213https://doi.org/10.1126/science.abj4213NiC-O ActivationGerry2-MarTRUE211452021Doyle, AG
Nickel-catalyzed cross-coupling reactions of 4-mesylcoumarins with aryl halides: Facile synthesis of 4-substituted coumarinsSCIENCE
A new and efficient nickel-catalyzed cross-coupling reaction between 4-mesylcoumarins and aryl halides was developed to give a number of 4-arylcoumarins in good yield under mild conditions. Unlike the previously reported coupling examples, this new method allows the direct cross-coupling of 4-mesylcoumarins with aryl- or vinyl halides in the NiCl2(PPh3)(2)/PPh3/Zn/toluene system. This has greatly facilitated the synthesis of biologically useful 4-substituted coumarins.
10/15/2021Csp3-ring(s)-Csp2_arE-NuOBOMeB(OH)2BenzylArylNo baseNo BaseStrong-0.28_10.1021/jacs.1c0839910.1039/d2sc00174h,10.1021/jacs.1c12198,10.1021/jacs.1c09718,10.1021/jacs.1c09718,10.1021/jacs.1c11503,10.1021/jacs.1c083993/10/2022
520
319FALSEscience.abo0039
10.1126/science.abo0039
https://sci-hub.wf/10.1126/science.abo0039https://doi.org/10.1126/science.abo0039NiC-O Activationx28-JulTRUE11#N/A2022
SCIENCECsp2_ar-Csp3E-EOXOTfBrArylAlkylNo baseNo BaseWeak0.53
521
77FALSEcl.15093610.1246/cl.150936https://sci-hub.wf/10.1246/cl.150936https://doi.org/10.1246/cl.150936NiC-O ActivationGerryTRUE4710892015Chatani, N
Univariate classification of phosphine ligation state and reactivity in cross-coupling catalysis
CHEMISTRY LETTERS
Chemists often use statistical analysis of reaction data with molecular descriptors to identify structurere-activity relationships, which can enable prediction and mechanistic understanding. In this study, we developed a broadly applicable and quantitative classification workflow that identifies reactivity cliffs in 11 Ni- and Pd-catalyzed cross-coupling datasets using monodentate phosphine ligands. A distinctive ligand steric descriptor, minimum percent buried volume [%V-bur (min)], is found to divide these datasets into active and inactive regions at a similar threshold value. Organometallic studies demonstrate that this threshold corresponds to the binary outcome of bisligated versus monoligated metal and that %V-bur (min) is a physically meaningful and predictive representation of ligand structure in catalysis.
Osaka Univ12/5/2015Csp2_ar-Csp3E-NuOAlOMeAlMe2ArylAlkylNaOtBuIonic-OtBuStrong-0.28_x10.1021/jacs.1c09797,10.1002/anie.201510497,10.1002/anie.201607646,10.1055/s-0036-1590863,10.1021/acs.joc.6b01627,10.1021/jacs.6b03253,10.1002/chem.201603436,10.1021/jacs.7b04279,10.1021/acscatal.7b01058,10.1021/acscatal.6b0080110.1021/jacs.1c09797,10.1039/d1qo00549a,10.1021/jacs.1c03038,10.1055/a-1467-2494,10.1021/acs.orglett.0c03507,10.1021/acs.chemrev.0c00088,10.1002/cjoc.201900506,10.1246/cl.200083,10.1002/jccs.201900450,10.1002/cctc.201900047,10.1007/3418_2018_19,10.1021/acs.orglett.8b01233,10.1038/s41467-018-03928-z,10.1021/acs.orglett.8b00847,10.1021/acs.orglett.8b00674,10.1002/cjoc.201700664,10.1021/acs.orglett.8b00080,10.1039/c7cy01205e,10.1055/s-0036-1590863,10.1055/s-0036-1589093,10.1055/s-0036-1588568,10.1021/acs.oprd.7b00241,10.1248/cpb.c17-00487,10.1021/jacs.7b04279,10.1021/acscatal.7b01058,10.1021/acs.orglett.6b03861,10.1246/bcsj.20160391,10.1002/anie.201610409,10.1021/jacs.6b10998,10.1021/acscatal.6b02964,10.1002/anie.201607646,10.1002/chem.201604160,10.1246/cl.160712,10.1002/chem.201603436,10.1021/acs.joc.6b01627,10.1002/asia.201600972,10.1007/s41061-016-0043-1,10.1021/acscatal.6b00801,10.1021/jacs.6b03253,10.1002/anie.201510497,10.3762/bjoc.12.65,10.1016/bs.adomc.2016.07.00112/28/2021
522
65FALSEcl.1986.40710.1246/cl.1986.407https://sci-hub.wf/10.1246/cl.1986.407https://doi.org/10.1246/cl.1986.407NiC-O ActivationKellyTRUE37301986
YAMASHITA, J
Nickel-catalyzed Cross-coupling of Anisole Derivatives with Trimethylaluminum through the Cleavage of Carbon Oxygen Bonds
CHEMISTRY LETTERS
Nickel-catalyzed cross-coupling of methoxyarenes with trimethylaluminum is described. The use of 1,3-dicyclohexylimidazol-2-ylidene as a ligand and (NaOBu)-Bu-t as a base promotes the methylation of anisole derivatives via the cleavage of normally unreactive aryl carbon oxygen bonds.
TOHOKU UNIV,FAC ENGN,DEPT APPL CHEM,ARAMAKI AOBA,SENDAI,MIYAGI 980,JAPAN.
3/1/1986Csp2_ar-Csp2_arE-EOOOTfOTfArylArylNo baseNo BaseWeak0.53_10.1021/jo00041a004,10.1021/jo00109a045,10.1021/jo00106a03110.1016/j.tet.2019.02.001,10.1039/c3cy00303e,10.1021/cr100259t,10.1016/S0040-4020(00)01018-8,10.1007/s007060070008,10.1006/jcat.2000.2865,10.1006/jcat.1999.2616,10.1039/a900181f,10.1002/jccs.199700033,10.1039/a608384f,10.1021/jo961464b,10.1080/00397919708006790,10.1021/jo00109a045,10.1021/jo00106a031,10.1080/00397919508015448,10.1021/jo00069a041,10.1016/0022-328X(92)80047-2,10.1021/jo00041a004,10.1021/ma00032a031,10.1246/cl.1991.2017,10.1021/jo00006a016,10.1246/bcsj.63.80,10.1039/p19890002513,10.1080/00397918908052600,10.1016/0022-328X(88)80176-1,10.1021/jo00241a017,10.1021/jo00226a030,10.3987/R-1987-02-0355,10.1246/nikkashi.1987.1972/14/2022
523
50FALSEcl.2005.79610.1246/cl.2005.796https://sci-hub.wf/10.1246/cl.2005.796https://doi.org/10.1246/cl.2005.796NiC-O ActivationKellyTRUE32212005Wu, J
ULTRASOUNDS IN SYNTHETIC REACTIONS .4. ULLMANN-TYPE COUPLING REACTION OF ARYL TRIFLUOROMETHANESULFONATES CATALYZED BY INSITU-GENERATED LOW VALENT NICKEL-COMPLEXES
CHEMISTRY LETTERS
Fudan Univ6/5/2005Csp2-Csp2_arE-NuOZnOTsZnXVinylArylNo baseNo BaseWeak0.36_x10.1002/adsc.201100151,10.1002/ejoc.20090006710.3987/REV-19-914,10.1021/acs.joc.5b00800,10.1002/adsc.201100151,10.1039/c1cs15100b,10.1002/chem.201002273,10.1055/s-0030-1258116,10.1016/j.tetlet.2009.10.096,10.1021/om900771v,10.1055/s-0029-1217067,10.3987/COM-09-11803,10.1002/ejoc.200900067,10.1002/jhet.96,10.1080/00397910802656026,10.1021/ol802049t,10.1016/j.ccr.2007.03.011,10.1039/b809577a,10.1021/ol702167t,10.1002/adsc.200700038,10.1021/cc070030z,10.1016/j.tetlet.2007.03.142,10.1002/adsc.200600527,10.1016/j.tetlet.2006.11.156,10.1016/j.tetlet.2006.10.156,10.1002/ejoc.200600469,10.1016/j.tetlet.2006.07.085,10.1246/cl.2006.562,10.1246/cl.2006.118,10.1039/b514635f,10.1039/b600540c,10.1055/s-2005-9171111/3/2022
524
578FALSEja909395610.1021/ja9093956https://sci-hub.wf/10.1021/ja9093956https://doi.org/10.1021/ja9093956NiC-X ActivationWilliam16-JulyTRUE1#N/A
Csp2_ar-Csp3XXXXArylAlkylNo baseNo Base7/28/2022
525
579FALSEja301769r10.1021/ja301769rhttps://sci-hub.wf/10.1021/ja301769rhttps://doi.org/10.1021/ja301769rNiC-X ActivationWilliam16-JulyTRUE1#N/A
Csp2_ar-Csp3XXBrBrArylAlkylNo baseNo Base7/28/2022
526
580FALSEja027433h10.1021/ja027433hhttps://sci-hub.wf/10.1021/ja027433hhttps://doi.org/10.1021/ja027433hCuC-X ActivationWilliamTRUE1#N/A
#N/AXHBrHNR2BenzylK3PO4Ionic-PO47/28/2022
527
581FALSEja301553c10.1021/ja301553chttps://sci-hub.wf/10.1021/ja301553chttps://doi.org/10.1021/ja301553cCuC-X ActivationxWilliamTRUE1#N/A
Csp2_ar-Csp3XBXB(OH)2ArylAlkylK2CO3Ionic-CO37/28/2022
528
582FALSEjo049658b10.1021/jo049658bhttps://sci-hub.wf/10.1021/jo049658bhttps://doi.org/10.1021/jo049658bCuC-X ActivationWilliamTRUE1#N/A
#N/AXHXHNR2ArylK3PO4Ionic-PO4
529
583FALSEol017186710.1021/ol0171867https://sci-hub.wf/10.1021/ol0171867https://doi.org/10.1021/ol0171867CuC-X ActivationTRUE1#N/A
Nsp3-Csp2_arXHXH
N(H)Aryl
ArylK3PO4Ionic-PO4
530
584FALSEol025773210.1021/ol0257732https://sci-hub.wf/10.1021/ol0257732https://doi.org/10.1021/ol0257732CuC-X ActivationTRUE1#N/A
Csp3-Csp2_arXHXHAlkylArylNo baseNo Base
531
585FALSEol035355c10.1021/ol035355chttps://sci-hub.wf/10.1021/ol035355chttps://doi.org/10.1021/ol035355cCuC-X ActivationTRUE1#N/A
Nsp3-Csp3XHBrH
N(Alkyl)Carbonyl
AlkylK2CO3Ionic-CO3
532
586FALSEs0040-4039(99)00291-9
10.1016/S0040-4039(99)00291-9
https://sci-hub.wf/10.1016/S0040-4039(99)00291-9https://doi.org/10.1016/S0040-4039(99)00291-9CuC-X ActivationTRUE1#N/A
#N/AXHXHNR2ArylCs2CO3Ionic-CO3
533
587FALSEol025548k
10.1021/ol025548k
https://sci-hub.wf/10.1021/ol025548khttps://doi.org/10.1021/ol025548kCuC-X ActivationTRUE1#N/A
Osp2-Csp2_arXHXHORArylCs2CO3Ionic-CO3
534
588FALSEanie.20060317310.1002/anie.200603173https://sci-hub.wf/10.1002/anie.200603173https://doi.org/10.1002/anie.200603173CuC-X ActivationTRUE1#N/A
Nsp3-Csp2_arXHXH
N(H)Aryl
ArylCs2CO3Ionic-CO3
535
589FALSEol005832g10.1021/ol005832ghttps://sci-hub.wf/10.1021/ol005832ghttps://doi.org/10.1021/ol005832gCuC-X ActivationTRUE1#N/A
Csp3-Csp2_arHBHB(OH)2AlkylArylNo baseNo BaseNu-H
536
590FALSEol000033j c
10.1021/ol000033j C
https://sci-hub.wf/10.1021/ol000033j Chttps://doi.org/10.1021/ol000033j CCuC-X ActivationTRUE1#N/A
Nsp3-Csp2_arHBHB(OH)2
N(H)Aryl
ArylNo baseNo BaseNu-H
537
591FALSEjo048599z 10.1021/jo048599z https://sci-hub.wf/10.1021/jo048599z https://doi.org/10.1021/jo048599z CuC-X ActivationTRUE1#N/A
Csp1-Csp2_arXHXHAlkyneArylNo baseNo Base
538
592TRUEja306062c10.1021/ja306062chttps://sci-hub.wf/10.1021/ja306062chttps://doi.org/10.1021/ja306062cNiC-H ActivationTRUE1#N/A
Csp2_ar-Csp2_arE-NuCsp2HCO2PhHArylHetK3PO4Ionic-PO411/22/2021
539
593FALSEol016821610.1021/ol0168216https://sci-hub.wf/10.1021/ol0168216https://doi.org/10.1021/ol0168216CuC-X ActivationTRUE1#N/A
#N/AXHXHNR2ArylCs2CO3Ionic-CO3
540
594FALSEjo102337710.1021/jo1023377https://sci-hub.wf/10.1021/jo1023377https://doi.org/10.1021/jo1023377CuC-Si ActivationFALSE1#N/A#N/A#N/A
541
595FALSEol016039610.1021/ol0160396https://sci-hub.wf/10.1021/ol0160396https://doi.org/10.1021/ol0160396CuN-H ActivationFALSE1#N/A#N/A#N/A
542
596FALSEja034201p10.1021/ja034201phttps://sci-hub.wf/10.1021/ja034201phttps://doi.org/10.1021/ja034201pCuC-X ActivationFALSE1#N/A#N/A#N/A
543
597FALSEja111249p10.1021/ja111249phttps://sci-hub.wf/10.1021/ja111249phttps://doi.org/10.1021/ja111249pCuC-H ActivationFALSE1#N/A#N/A#N/A
544
598FALSEscience.125552510.1126/science.1255525https://sci-hub.wf/10.1126/science.1255525https://doi.org/10.1126/science.1255525NiDecarbonylx20-JulyTRUE1#N/A
Csp3-Csp2_arCsp2XCOOHBrAlkylArylCs2CO3Ionic-CO37/28/2022
545
599FALSEjo00430a04110.1021/jo00430a041https://sci-hub.wf/10.1021/jo00430a041https://doi.org/10.1021/jo00430a041NiC-X ActivationWilliam20-JulyTRUE1#N/A
Csp2_ar-Csp2_arXZnBrZnXArylArylNo baseNo Base7/28/2022
546
600FALSEscience.125364710.1126/science.1253647https://sci-hub.wf/10.1126/science.1253647https://doi.org/10.1126/science.1253647NiC-X ActivationxWilliam20-JulyTRUE1#N/A
Csp3-Csp2_arXBBrBF3KAlkylArylNo baseNo Base7/28/2022
547
601FALSE0040-4020(82)80117-810.1016/0040-4020(82)80117-8https://sci-hub.wf/10.1016/0040-4020(82)80117-8https://doi.org/10.1016/0040-4020(82)80117-8NiC-X ActivationWilliam20-JulyTRUE1#N/A
Csp3-Csp3XMgXMgXAlkylAlkylNo baseNo Base7/28/2022
548
602FALSEbcsj.49.195810.1246/bcsj.49.1958https://sci-hub.wf/10.1246/bcsj.49.1958https://doi.org/10.1246/bcsj.49.1958NiC-X ActivationWilliam20-JulyTRUE1#N/A
Csp3-Csp2_arXMgClMgXAlkylArylNo baseNo Base7/28/2022
549
603FALSEpac19805203066910.1351/pac198052030669https://sci-hub.wf/10.1351/pac198052030669https://doi.org/10.1351/pac198052030669NiC-X ActivationWilliam20-JulyTRUE1#N/A
Csp3-Csp2_arXMgClMgXAlkylArylNo baseNo Base7/28/2022
550
215FALSEcl.2009.71010.1246/cl.2009.710https://sci-hub.wf/10.1246/cl.2009.710https://doi.org/10.1246/cl.2009.710NiC-O ActivationLongTRUE13134892009Chatani, N
Efficient route to 4-substituted-2(5H)-furanones, 2(1H)-quinolones, and pyrones by nickel-catalyzed cross-coupling of arenesulfonates with organozinc reagents
CHEMISTRY LETTERS
Nickel (II)-catalyzed cross-coupling reactions of 4-tosyl-2(1H)-quinolone, pyrone, and 2(5H)-furanone with various organozinc reagents provide an efficient and practical method for the high-yielding synthesis of 4-substituted 2(1H)-quinolones, pyrones, and 2(5H)-furanones.
Osaka Univ7/5/2009Csp2_ar-Nsp3E-NuOHOMeHAryl
Morpholine
NaOtBuIonic-OtBuStrong-0.28_xx10.1021/ja210249h,10.1002/chem.201605095,10.1021/acscatal.8b01879,10.1002/anie.201007325,10.1021/acscatal.6b00801,10.1002/anie.201510497,10.1021/jacs.7b04973,10.1021/om300566m,10.1002/anie.201410875,10.1002/chem.201603436,10.1021/ol4011757,10.1002/anie.200907359,10.1021/jacs.7b02326,10.1021/ol203322v,10.1021/ol502583h,10.1021/ja200398c,10.1039/c1sc00230a,10.1002/anie.201806790,10.1021/jacs.9b02751,10.1021/jacs.1c09797,10.1021/ol201437g,10.1021/ol503707m,10.1021/ol901978e,10.1002/anie.201607646,10.1002/chem.201103784,10.1021/ol301847m,10.1021/acs.orglett.5b02200,10.1021/acscatal.6b00865,10.1246/cl.150936,10.1021/ol403209k,10.1016/j.tet.2012.04.005,10.1021/acs.orglett.7b00556,10.1021/ol302112q,10.1021/cs501045v10.1021/acs.inorgchem.1c02127,10.1021/jacs.1c09797,10.1039/d1qo00549a,10.1021/acs.orglett.1c00313,10.1021/acs.joc.0c02350,10.1021/acs.chemrev.0c00088,10.1002/cjoc.201900506,10.1246/cl.200083,10.1246/cl.200099,10.1055/s-0039-1690010,10.1002/chem.201904288,10.1021/acs.orglett.9b01805,10.1055/s-0037-1611732,10.1002/anie.201902315,10.1002/cjoc.201800575,10.1002/chem.201900498,10.1021/acs.organomet.8b00720,10.1007/3418_2018_19,10.1039/c8cc03665a,10.1002/anie.201806790,10.1021/acscatal.8b01879,10.1021/acs.orglett.8b01696,10.1021/acs.organomet.8b00046,10.1021/acs.orglett.8b00674,10.1002/aoc.4273,10.1021/acs.orglett.8b00060,10.1021/acs.orglett.8b00080,10.1039/c7cc08709h,10.1039/c7cy01205e,10.1002/chem.201703266,10.1055/s-0036-1589093,10.1055/s-0036-1588568,10.1055/s-0036-1590962,10.1021/jacs.7b04973,10.1039/c7ob01791j,10.1007/s11172-017-1920-7,10.1021/acs.orglett.7b01549,10.1021/jacs.7b02326,10.1021/acs.joc.6b02701,10.1021/acs.orglett.7b00556,10.1002/anie.201611819,10.1016/j.cclet.2016.11.002,10.1246/bcsj.20160391,10.1016/j.jorganchem.2016.12.029,10.1002/anie.201610409,10.1021/jacs.6b10998,10.1021/acscatal.6b02964,10.1002/chem.201605095,10.1002/anie.201607646,10.1002/ajoc.201600411,10.1246/cl.160712,10.1002/chem.201603436,10.1002/tcr.201500305,10.1007/s41061-016-0043-1,10.1002/adsc.201600590,10.1021/acscatal.6b00801,10.1021/acscatal.6b00865,10.1002/anie.201510497,10.1016/j.tet.2016.02.069,10.1016/j.jorganchem.2016.02.018,10.1021/acscatal.5b02058,10.1021/acscatal.5b02021,10.1002/anie.201509133,10.1016/bs.adomc.2016.07.001,10.1246/cl.150936,10.1021/jacs.5b08621,10.1021/acs.orglett.5b02200,10.1002/ejoc.201500630,10.1021/acs.orglett.5b01229,10.1016/j.tet.2015.02.088,10.1021/jacs.5b03955,10.1021/acs.accounts.5b00051,10.1002/ejoc.201500226,10.1002/anie.201410875,10.1246/cl.141084,10.1021/cs501498f,10.1021/ja512498u,10.1021/ol503707m,10.1016/j.molcata.2014.10.031,10.1039/c5qo00039d,10.1039/c5nj01354b,10.1039/c5sc00305a,10.3998/ark.5550190.p008.915,10.1021/ol502583h,10.1021/cs501045v,10.1002/anie.201404355,10.1002/adsc.201400201,10.1021/ja412107b,10.1021/ol403209k,10.1039/c3ob42053a,10.1039/c4cs00206g,10.1021/ol4011757,10.1021/ja312464b,10.1007/3418_2012_42,10.1039/c3sc22242j,10.1002/anie.201208843,10.1021/op300236f,10.1016/j.tetlet.2012.08.015,10.1002/adsc.201200364,10.1021/om300566m,10.1021/ol302112q,10.1021/ol301847m,10.1016/j.tet.2012.04.005,10.1021/ol3009842,10.1021/ol203322v,10.1002/chem.201103784,10.1021/ol2033306,10.1021/ja210249h,10.1246/cl.2011.1001,10.1002/cctc.201100181,10.1021/ol201437g,10.1021/ja200398c,10.1021/cr100259t,10.1002/anie.201007325,10.1039/c0cc05169a,10.1039/c1sc00230a,10.1002/chem.201001943,10.1002/chem.201002273,10.1016/j.jorganchem.2010.08.047,10.1021/ja106943q,10.1016/S1872-2067(09)60089-9,10.1002/anie.200907359,10.1021/ol901978eKelly12/2/2021
551
606FALSEacscatal.5b0220410.1021/acscatal.5b02204https://sci-hub.wf/10.1021/acscatal.5b02204https://doi.org/10.1021/acscatal.5b02204NiC-X Activationx21-JulyTRUE1#N/A
Csp2_ar-Csp3XCsp2xCOOHArylAlkylNo baseNo Base7/28/2022
552
607FALSEnature1487510.1038/nature14875https://sci-hub.wf/10.1038/nature14875https://doi.org/10.1038/nature14875NiC-X Activationx22-JulyTRUE1#N/A
Csp2_ar-Csp3-ring(s)XHXHAryl
Csp3-(Aryl)(OR)
K2CO3Ionic-CO37/28/2022
553
608FALSEol071248x10.1021/ol071248xhttps://sci-hub.wf/10.1021/ol071248xhttps://doi.org/10.1021/ol071248xNiNot suitable reaction (C-S coupling)22-JulyFALSE1#N/A#N/A#N/A
554
609FALSEjacs.5b1321110.1021/jacs.5b13211https://sci-hub.wf/10.1021/jacs.5b13211https://doi.org/10.1021/jacs.5b13211NiC-X Activationx22-JulyTRUE1#N/A
Csp2_ar-Csp2_arXCsp2xCOOHArylArylNo baseNo Base7/28/2022
555
610FALSEja00437a06710.1021/ja00437a067https://sci-hub.wf/10.1021/ja00437a067https://doi.org/10.1021/ja00437a067NiC-X Activation22-JulyFALSE1#N/A#N/A#N/A
556
611FALSEja511913h10.1021/ja511913hhttps://sci-hub.wf/10.1021/ja511913hhttps://doi.org/10.1021/ja511913hNiC-X Activationx22-JulyTRUE1#N/A
Csp2-Csp3XCsp2XCOOHVinylAlkylNo baseNo Base7/28/2022
557
612FALSEj.cclet.2022.01.077
10.1016/j.cclet.2022.01.077
https://sci-hub.wf/10.1016/j.cclet.2022.01.077https://doi.org/10.1016/j.cclet.2022.01.077NiC-X Activation22-JulyTRUE1#N/A
Csp2_ar-Csp3XXXXArylAlkylNo baseNo Base7/28/2022
558
613FALSEejoc.202200214
10.1002/ejoc.202200214
https://sci-hub.wf/10.1002/ejoc.202200214https://doi.org/10.1002/ejoc.202200214NiC-H Activation22-JulyFALSE1#N/A#N/A#N/A
559
614FALSEacscatal.0c05484
10.1021/acscatal.0c05484
https://sci-hub.wf/10.1021/acscatal.0c05484https://doi.org/10.1021/acscatal.0c05484NiReview article22-JulyFALSE1#N/A#N/A#N/A
560
615FALSEja210364r10.1021/ja210364rhttps://sci-hub.wf/10.1021/ja210364rhttps://doi.org/10.1021/ja210364rNiNot suitable reaction (C-S coupling)23-JulyFALSE1#N/A#N/A#N/A
561
616TRUEanie.20170790610.1002/anie.201707906https://sci-hub.wf/10.1002/anie.201707906https://doi.org/10.1002/anie.201707906NiC-X Activationx25-JulTRUE1#N/A
Csp2_ar-Csp3XHXHArylAlkylNo baseNo Base7/28/2022
562
617FALSEacscatal.9b0178510.1021/acscatal.9b01785https://sci-hub.wf/10.1021/acscatal.9b01785https://doi.org/10.1021/acscatal.9b01785NiC-X Activationx25-JulFALSE1#N/A#N/A#N/A
563
618FALSEjacs.0c0147510.1021/jacs.0c01475https://sci-hub.wf/10.1021/jacs.0c01475https://doi.org/10.1021/jacs.0c01475NiC-X Activationx25-JulTRUE1#N/A
Csp2_ar-Csp3XXXXArylAlkylNo baseNo Base7/28/2022
564
619FALSEanie.20201424410.1002/anie.202014244https://sci-hub.wf/10.1002/anie.202014244https://doi.org/10.1002/anie.202014244NiC-X ActivationxTRUE1#N/A
Csp2_ar-Csp3-ring(s)XBXBF3KArylBenzylNo baseNo Base7/28/2022
565
620FALSEja00232a03010.1021/ja00232a030https://sci-hub.wf/10.1021/ja00232a030https://doi.org/10.1021/ja00232a030NiC-X Activation25-JulyFALSE1#N/A#N/A#N/A
566
621FALSEchem.202103486
10.1002/chem.202103486
https://sci-hub.wf/10.1002/chem.202103486https://doi.org/10.1002/chem.202103486NiC-C Activation25-JulyFALSE1#N/A#N/A#N/A
567
622FALSEja407589e10.1021/ja407589ehttps://sci-hub.wf/10.1021/ja407589ehttps://doi.org/10.1021/ja407589eNiReview articlex26-JulFALSE1#N/A#N/A#N/A
568
623FALSEja30406810.1021/ja304068https://sci-hub.wf/10.1021/ja304068https://doi.org/10.1021/ja304068NiWrong DOI26-JulFALSE1#N/A#N/A#N/A
569
624FALSEja909689t10.1021/ja909689thttps://sci-hub.wf/10.1021/ja909689thttps://doi.org/10.1021/ja909689tNiC-X Activation26-JulTRUE1#N/A
Csp3-Csp2_arXMgXMgXAllylArylNo baseNo Base7/28/2022
570
625TRUEanie.20170790610.1002/anie.201707906https://sci-hub.wf/10.1002/anie.201707906https://doi.org/10.1002/anie.201707906NiC-X Activationx26-JulTRUE1#N/A
Csp2_ar-Csp3XHXHArylAlkylNo baseNo Base7/28/2022
571
626FALSEja5080610.1021/ja50806https://sci-hub.wf/10.1021/ja50806https://doi.org/10.1021/ja50806NiWrong DOI26-JulFALSE1#N/A#N/A#N/A
572
627FALSEjacs.9b0188610.1021/jacs.9b01886https://sci-hub.wf/10.1021/jacs.9b01886https://doi.org/10.1021/jacs.9b01886NiC-X Activationx26-JulTRUE1#N/A
#N/AXHXHArylNR2No baseNo Base7/28/2022
573
628FALSEanie.20191275310.1002/anie.201912753https://sci-hub.wf/10.1002/anie.201912753https://doi.org/10.1002/anie.201912753NiC-X ActivationxLong26-JulTRUE1#N/A
Csp2_ar-Csp3XXXXArylAlkylNo baseNo Base7/28/2022
574
629FALSEchem.202103643
10.1002/chem.202103643
https://sci-hub.wf/10.1002/chem.202103643https://doi.org/10.1002/chem.202103643NiC-H ActivationLong26-JulTRUE1#N/A
Csp2-Csp2_arHAlH
Al(iBu)2
VinylArylNo baseNo BaseNu-H7/28/2022
575
630FALSEa-1337-5504
10.1055/a-1337-5504
https://sci-hub.wf/10.1055/a-1337-5504https://doi.org/10.1055/a-1337-5504NiNot suitable reaction (two formed bodn)26-JulFALSE1#N/A#N/A#N/A
576
631FALSEanie.201611819
10.1002/anie.201611819
https://sci-hub.wf/10.1002/anie.201611819https://doi.org/10.1002/anie.201611819NiNot suitable reaction (break double bond)26-JulFALSE1#N/A#N/A#N/A
577
54FALSEcl.2011.100110.1246/cl.2011.1001https://sci-hub.wf/10.1246/cl.2011.1001https://doi.org/10.1246/cl.2011.1001NiC-O ActivationShihongTRUE3410482011Xi, ZF
Ni-0-catalyzed Direct Amination of Anisoles Involving the Cleavage of Carbon-Oxygen Bonds
CHEMISTRY LETTERS
Ni-0-catalyzed cross-coupling of aryl methyl ethers with amines is described. The use of an N-heterocyclic carbene as a ligand and NaOt-Bu as a base promotes the amination of anisole derivatives via the cleavage of normally unreactive aryl carbon-oxygen bonds.
Peking Univ9/5/2011Csp2_ar-Csp2_arE-NuOMgOTMSMgXArylArylNo baseNo BaseStrong-0.27_10.1021/ol503707m,10.1002/anie.201806790,10.1021/ol4011757,10.1021/ol502583h,10.1021/acs.orglett.5b02200,10.1002/chem.201603436,10.1246/cl.150936,10.1021/ol302112q,10.1021/acscatal.7b01058,10.1021/ja307045r10.1021/acscatal.1c01077,10.1055/a-1349-3543,10.1055/s-0040-1705986,10.1021/acscatal.0c03334,10.1021/acs.chemrev.0c00088,10.1007/s00706-019-2364-6,10.1007/3418_2018_19,10.1021/acs.joc.8b02104,10.1002/anie.201806790,10.1051/e3sconf/20183804026,10.1021/acscatal.7b02025,10.1248/cpb.c17-00487,10.1021/acscatal.7b01058,10.1246/cl.160712,10.1002/chem.201603436,10.1007/s41061-016-0043-1,10.1016/bs.adomc.2016.07.001,10.1246/cl.150936,10.1002/chem.201502114,10.1021/acs.orglett.5b02200,10.1021/ol503707m,10.1039/c5qo00039d,10.1039/C5QO00243E,10.1021/ol502583h,10.1016/j.ica.2014.08.012,10.1002/chem.201404380,10.1021/ja410883p,10.1021/ol4011757,10.1002/ejoc.201300102,10.1039/c3ra44884c,10.1021/ja307045r,10.1021/ol302112q12/22/2021
578
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Cross-coupling of Aryl/Alkenyl Silyl Ethers with Grignard Reagents through Nickel-catalyzed C-O Bond Activation
CHEMISTRY LETTERS
C-O activation and its application have drawn much attention since oxygen-based electrophiles are easily available, less toxic, and more environmentally benign. This letter presents systematically results on the Ni-catalyzed Kumada-Tamao-Corriu coupling based on siloxy arenes/alkenes, which provides a new strategy of silyl protection/C-C bond formation sequence in organic synthesis.
Kyushu Univ9/5/2011Csp2_ar-Csp2_arE-NuOB
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